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Review

One-Pot Multicomponent Polymerization, Metal-, and Non-Metal-Catalyzed Synthesis of Organoselenium Compounds

by
Saad Shaaban
1,2,*,
Hany M. Abd El-Lateef
1,3,
Mai M. Khalaf
1,3,
Mohamed Gouda
1 and
Ibrahim Youssef
2,4,5,*
1
Department of Chemistry, College of Science, King Faisal University, P.O. Box 380, Al-Ahsa 31982, Saudi Arabia
2
Department of Chemistry, Organic Chemistry Division, College of Science, Mansoura University, Mansoura 11432, Egypt
3
Chemistry Department, Faculty of Science, Sohag University, Sohag 82524, Egypt
4
Transcranial Focused Ultrasound Laboratory, UTSW Medical Center, Dallas, TX 75390, USA
5
Neuroradiology and Neuro-Intervention Section, Department of Radiology, UTSW Medical Center, Dallas, TX 75390, USA
*
Authors to whom correspondence should be addressed.
Polymers 2022, 14(11), 2208; https://doi.org/10.3390/polym14112208
Submission received: 16 May 2022 / Revised: 26 May 2022 / Accepted: 27 May 2022 / Published: 29 May 2022
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Abstract

:
The one-pot multicomponent synthetic strategy of organoselenium compounds represents an alternative and robust protocol to the conventional multistep methods. During the last decade, a potential advance has been made in this domain. This review discusses the latest advances in the polymerization, metal, and metal-free one-pot multicomponent synthesis of organoselenium compounds.

1. Introduction

Organoselenium (OSe) compounds have recently gained considerable interest as a potential class of organic motifs due to their outstanding applications in synthetic organic and medicinal chemistry and their possible properties in materials science [1,2,3,4]. These are attributed to the exceptional properties of the selenium (Se) element. The latter is a non-metal present in almost living organisms as part of selenoproteins (e.g., thioredoxin reductases and glutathione peroxidase antioxidants enzymes) [5,6,7,8,9]. Accordingly, Se is crucial for protecting human cells from oxidative damage and the immune system’s normal function [10,11,12]. Compared to sulfur (S), Se has a larger atomic radius (S: 1.02 Å vs. Se: 1.17 Å), lower electronegativity (S: 2.58 vs. Se: 2.55), higher polarizability (S: 2.9 Å vs. Se: 3.8 Å), and therefore Se is a likely better nucleophile than the S [5,8,13]. Accordingly, OSe compounds are known for their ability to react with O2-free radicals and thus prevent the progression of oxidative stress-related diseases [3,6,10,14]. Furthermore, OSe compounds were also used in material science due to their semiconductor potential and therefore used in sodium-ion batteries, solar cells, and H2 evolution catalysts [2,15,16,17]. Moreover, the Se center is present in many naturally occurring and bioactive interesting OSe compounds (Figure 1), such as the selenoaminoacids (e.g., selenocysteine (I), selenomethionine (II), and selenocystine (III)) [18,19,20]. Furthermore, ebselen (IV) is the most investigated Se compound with exciting GPX-like activity and has recently reached clinical phase III trials as a possible drug for Meniere’s disease [11,21,22] (Figure 1). Moreover, ethaselen (V) entered trial phase II for non-small lung cancer treatment [23,24,25,26]. On the other hand, different OSe compounds have also manifested efficient catalytic activity for various organic reactions, such as the palladium-based OSe complex VI for the Heck reaction (Figure 1) [27].
Given the exciting activities and the diverse applications of the OSe compounds, sustainable and efficient approaches for their preparation are in high demand. The synthesis of OSe compounds depends on their chemical structures (e.g., selenides, selenocyanates, diselenides) [26,28,29]. Standard methods include direct selenylation via reaction with proper Se reagents such as Na2Se2 and KSeCN. On the other hand, indirect selenylations include rearrangement of Se-containing precursors (e.g., isoselenocyanates) or multistep synthetic procedures using elemental Se together with organolithium or Grignard reagents and [2,13,24,30,31,32,33,34,35]. Despite being efficient, these classical strategies are relatively limited due to the challenges associated with the complicated synthetic procedure, regioselectivity, or harsh reaction conditions issues. Recently, various alternative reactions were developed as efficient and milder synthetic protocols within combinatorial chemistry (CC) [36,37,38,39,40,41,42,43]. The latter has emerged as a robust tool in medicinal chemistry [44,45]. It is now widely and consecutive covalent bonds formed between different building blocks [46]. Concurrently, drug candidates are discovered and selected by the screening of small molecule libraries for particular biological targets [47]. Despite the various strategies used in CC, multicomponent reactions (MCRs) are amongst the most investigated techniques for the efficient synthesis of chemical libraries [43,45]. MCRs have been known for over a century. They include generating skeletally diverse and complex molecular entities from more than two starting materials by straightforward chemical transformations employing comparatively mild conditions [37,48,49,50].
From an economical step and atom viewpoint, the MCR one-pot strategy would offer more robust access to OSe compounds. Though the MCRs have emerged as an efficient tool for constructing C-S bonds, similar approaches for synthesizing C-Se bonds have recently attracted more attention. We here want to summarize the recent developments of OSe compounds using the MCR one-pot approach to pave the way for medicinal chemists to have more accessible synthetic access to such a biologically relevant category of compounds. Specifically, we have structured this review based on the developments in metal-catalyzed and metal-free reactions in addition to the multicomponent polymerization synthesis of OSe compounds.

2. The One-Pot Multicomponent Combinatorial Synthesis of OSe Compounds

2.1. Metal-Catalyzed Synthesis of the OSe Compounds

In 2013, de Oliveira et al. reported the one-pot Cu-catalyzed (CuCl) synthesis of OSe propargylamines in excellent yields (up to 95%) via A3-coupling of trimethylsilyl Se-acetylene, p-methoxybenzaldehyde, and piperidine catalyzed in DCM as the solvent and in the presence of succinic acid additive at 50 °C (Scheme 1) [51].
In 2017, Liu et al. reported the synthesis of highly functionalized isoselenoureas through the Cu-catalyzed (CuI) 1,10-phenanthroline-promoted MCR of elemental Se, aryl iodides, isocyanides, and amines using Cs2CO3 as the base and THF as the solvent at 70 °C (Scheme 2) [52].
In 2018, Aquino et al. synthesized (arylselanyl)-alkyl-1,2,3-triazolo-1,3,6-triazonines via CuI-catalyzed MCR of 2-azidobenzaldehyde, 1,2-diaminobenzene, and various arylchalcogenyl alkynes in dioxane at 100 °C. The reaction included a wide variety of arylchalcogenyl alkynes (Scheme 3) [53].
Zhang et al. reported the sequential multistep Cu-catalyzed (CuI) assembly of 5-selenotriazoles via the one-pot reaction of elemental Se, azide, alkyl halide, and alkyne. The selenylating agent and Cu(I) triazolides were generated in situ, and the reaction proceeded under mild conditions using readily available substrates with broad variety scope in high regioselectivity (Scheme 4) [54].
In 2019, Gao et al. reported the Cu-catalyzed (Cu(OAc)2) cross-coupling oxidative aminoarylselenation of maleimides using elemental Se, aryl iodides, and secondary amines. This reaction enabled the bifunctionalization of alkenes via the simultaneous one-pot construction of the C−N bond and C−Se bonds (Scheme 5) [55].
Recently, Begini et al. developed 4-arylselanyl-1H-1,2,3-triazoles from the one-pot Cu-catalyzed (Cu(OAc)2) reaction of selanylalkynylcarbinols and aryl azides in the presence of sodium ascorbate (10 mol%) in H2O and THF (1:1) mixed solvent at 50 °C (Scheme 6) [56].
In 2021, Rather et al. disclosed the Cu-catalyzed (CuBr) synthesis of 3-((arylethynyl)selanyl)-1H-indoles in good yield (up to 83%) from elemental Se phenylacetylene and indole using K2CO3 as the base and DMSO as the solvent at 100 °C. The strategy tolerates different indoles and phenylacetylene motifs and can be expanded to a gram scale without any difficulties (Scheme 7) [57].
Furthermore, Lara et al. reported the synthesis of (Z)-1,2-bis-arylselanyl alkenes by the one-pot reaction of terminal alkynes with diaryl diselenides using KF/Al2O3 and PEG-400 as a solvent in good yields. Interestingly, the reaction time was reduced from 6 h under conventional conditions to 30 min using microwave irradiation (Scheme 8) [58].
De Oliveira et al. reported the ytterbium(III)-catalyzed (Yb(OTf)3) synthesis of 2,4- disubstituted Se-quinoline derivatives via Povarov MCR between ethyl glyoxylate, p-anisidine, and ethynyl(phenyl)selane in CH3CN as the solvent at 80 °C and in moderate yields (up to 69%) (Scheme 9) [59].
Moreover, Sakai et al. reported the indium-catalyzed (InCl3/PhSiH3) one-pot synthesis of selenolactones from elemental Se and lactones using o-dichlorobenzene as the solvent at 120 °C for 24 h (Scheme 10) [60].
Recently, Attia et al. reported the one-pot synthesis of seleno [2,3-b]pyridine derivatives using Ag/AgCl nanoparticles under visible light irradiation. The reaction was carried out under mild conditions using visible light as the energy source, Ag/AgCl- nanoparticles, and EtOH as the solvent. It is worth noting that the Ag/AgCl- nanoparticles showed high catalytic activity and reusability potential up to five cycles in 94–91% isolated yields (Scheme 11) [61].
Recently, the same group by Abdel-Hafez et al. reported the synthesis of selenopyridine and quinoline derivatives in excellent yields (up to 90%) and selectivity using Co3O4 nanoparticles heterogeneous catalyst under microwave irradiation and water as the solvent (Scheme 12) [62].

2.2. Metal-Free Synthesis of the OSe Compounds

In 2010, Artem’ev et al. reported the MCR one-pot synthesis of alkylammonium diselenophosphinates in excellent yield (up to 97%) via reaction of elemental Se with amines (e.g., primary, secondary, or tertiary) and secondary phosphines in ethanol at 60 °C (Scheme 13) [63].
Furthermore, Artem’ev et al. also synthesized diselenophosphinates via a three-component reaction of secondary phosphine, Se powder, and amines in ethanol at 50–75 °C for 30 min (Scheme 14) [64].
Additionally, Artem’ev et al. reported the one-pot multicomponent synthesis of mono-, di-, and trialkylammonium thioselenophosphinates in good yields (up to 94%) from secondary phosphanes, amines (primary, secondary, or tertiary), elemental S, and elemental Se (Scheme 15) [65].
Despite the high yield and considerable success of the above reaction, it was limited to certain amines such as triethyl amine, dipropyl amine, and diisopropylamine. In 2012, Artem’ev et al. extended this reaction to natural alkaloids of different N-bases, namely, lupinine, anabasine, and quinine [66] (Scheme 16).
De La Torre et al. reported the metal-free synthesis of new selenocysteine-based peptoids and peptide–peptoid conjugates. The latter includes organocatalytic insertion of phenylselenium into the backbone of the aldehyde moiety using Jørgensen’s catalyst, followed by a subsequent Ugi reaction (Scheme 17) [67].
In 2018, Singh et al. reported the one-pot synthesis of 5-aryl-1,3-dimethyl-7-selenoxopyrimidino [4,5-d]pyrimidine-2,4(1H,3H)-diones in good yields (up to 82%) by the reaction of aroyl chloride, KSeCN and 6-amino-N,N′-dimethyluracil in acetone (Scheme 18) [68].
Liu et al. reported the multicomponent Se functionalization of indoles at the C3 under transition metal-free conditions. The reaction was carried out using elemental Se, isocyanides, amines, and indoles. The reaction proceeded under mild conditions employing O2 as the oxidant and TEMPO as the catalyst and encompassed a wide range of substrates in moderate to high yields (Scheme 19) [69].
In 2020, Liu et al. reported the one-pot synthesis of 2-amino-1,3-selenazoles with transition metal-free MCR of elemental Se, amines, and α,β-unsaturated isocyanides. The reaction of the elemental Se with isocyanide affords the corresponding isoselenocyanate, which undergoes intramolecular Michael cycloaddition followed by aromatization to provide 2-amino-1,3-selenazole in good yields (up to 80%) (Scheme 20) [70].
In 2020, Zhao et al. reported the organocatalytic (N-fluorobenzenesulfonimide) one-pot synthesis of 3-selenylindoles through intramolecular cyclization/selenylation of 2-vinylaniline in moderate to good yield (up to 88%). The reaction was smoothly furnished, employing wide substrates and good functional group transformations, and could also be tolerated to gram scale (Scheme 21) [71].
In 2022, Liu et al. reported the metal-free MCR synthesis of 3-alkylselenindole derivatives from elemental Se, indoles, and unactivated alkyl halides under mild conditions using t-BuONa as the base in CH3CN as the solvent at 40 °C. The reaction encompassed wide functional group tolerance and can also be applied for a large scale (>10 g) in excellent yield (>90% yield) (Scheme 22) [72].
In 2021, Li et al. reported the synthesis of diselenocarbamates in good yields (up to 91%) via the one-pot MCR of elemental Se, amines, diselanes, and CHCl3 using t-BuOK as the base and NMP as the solvent at 50 °C for 12 h (Scheme 23) [73].
Fang et al. developed the base promoted and metal-free cascade synthesis of 2-aminobenzo[d][1,3]selenazines via reaction of elemental Se, ortho-functionalized aryl isocyanides, and amines. The reaction proceeded under basic conditions via the in situ formation of isoselenocyanates from elemental Se and subsequent intramolecular Michael addition reactions (Scheme 24) [74].
Additionally, Fang et al. reported the metal-free preparation of 1,2,4-selenadiazol-5-amine derivatives in moderate to excellent yields (up to 96%) through the aerobic radical-cascade reactions of Se powder, isocyanides, and imidamides using O2 as the green oxidant. It is worth noting that the reaction H2O was the only byproduct obtained and the reaction encompassed good functional group tolerance and broad substrate scope. In addition, this protocol was applied for the late-stage functionalization of biologically active candidates (Scheme 25) [75].
Heredia et al. synthesized alkynyl selenides in moderate to good yields under aerobic metal-free conditions from the reaction of KSeCN, alkyl halides, and terminal alkynes using PEG 200 as the solvent. In this reaction, dialkyl diselenides were formed in situ from the K3PO4-assisted reaction of alkyl halides and KSeCN with terminal alkynes in the presence of t-BuOK (Scheme 26) [76].
In 2013, Prabhu et al. reported the metal-free one-pot synthesis of phenylseleno N-acetyl amino acids from amino acids, chloroacetyl, and NaSePh in H2O: EtOH (2:1) mixed solvent (Scheme 27) [77].
Armstrong et al. reported the synthesis of trisubstituted allylic selenides via an asymmetric, organocatalytic α-selenenylation of aldehydes using N-(phenylseleno)phthalimide followed by Horner–Wadsworth–Emmons olefination using and phosphonate anions (Scheme 28) [78].
Pan et al. reported the one-pot, metal-free, and solvent-free synthesis of diselenocarbamates from the reaction of CSe2, alkyl halides, and amines at −10 °C (Scheme 29) [79].
Furthermore, diselenocarbamates were synthesized from CSe2 with aliphatic amines and alkenes as electron-deficient substrates via Michael-type addition using silica gel as the media (Scheme 30) [79].
Ahn et al. reported the one-pot preparation of organoselanyltrifluoroborates from Se powder, dihalobenzenes, and alkyl halides in 56–92% yields using n-BuLi and boron isopropoxide at −78 °C (Scheme 31) [80].
In 2021, Sands et al. reported the one-pot synthesis of structurally diverse selenonic acids in good yields (up to 90%) from elemental Se and aryl bromides. The reaction involves metalation using t-Butyllithium, selenation, and oxidation using H2O2, followed by ion exchange using Rexyn 101(H) ion-exchange resin (Scheme 32) [81].
In 2020, Wu et al. disclosed the one-pot multicomponent synthesis of unsymmetrical selenoureas and cycloselenoureas from selenium powder, CHCl3, and two different amines using t-BuOH as the base at 50 °C for 3 h in moderate–good yields (up to 86%) (Scheme 33) [82].
In 2022, Shaaban and colleagues reported the development of urea-based selenocyanates and symmetrical diselenides in good yields (up to 93%) using 4-selenocyanatoaniline and 4,4′-diselanediyldianiline, respectively, and commercially available isocyanates in toluene (Scheme 34) [83].
In 2021, Shaaban et al. and his group developed of peptide-like and tetrazole-based redox-active multifunctional OSe compounds via multicomponent Ugi and azido-Ugi reactions. The reaction included novel Se-based aniline building blocks to incorporate the Se redox center into the backbone of the Ugi/Ugi-azide structurally diverse product’s tail. Indeed, the reactions were carried out under mild conditions using DCM and MeOH as the solvent for the Ugi and Azido-Ugi reactions, respectively (Scheme 35) [12].
Furthermore, Shaaban et al. reported the combinatorial one-pot synthesis of tetrazole-based symmetrical diselenides and selenoquinones compounds via azido-Ugi and sequential nucleophilic substitution methodology (Scheme 36) [84].
Moreover, Shaaban et al. also reported the synthesis of different Se peptidomimetic compounds employing the Ugi isocyanide-based MCR using the Se-based isonitrile 3-isocyanopropyl(phenyl)selane. The reaction was achieved under mild conditions using H2O as the solvent in good yields (up to 94%) (Scheme 37) [85].
Additionally, Shaaban et al. reported the synthesis of symmetrical diselenide via one-pot Ugi using 4-(2-(4-aminophenyl)diselanyl)benzenamine as key synthon, which in turn allowed the access to the diselenide scaffolds (Scheme 38) [86].
In 2021, Shaaban et al. reported the synthesis of new selenocyanate isocyanide and diselenide diisonitrile and explored their reactivities in Passerini, Ugi, and Azido-Ugi reactions. OSe-based pseudopeptides, peptidomimetics, and tetrazoles were obtained in good yields (up to 94%) (Scheme 39) [87].
Chang et al. reported the three components regioselective one-pot synthesis of chiral 2-iminoselenazolines by sonication from L-aminoester, isoselenocyanate, and α-bromoketone. In this reaction, selenazoles are obtained by Hantzsch reaction of selenoureas, generated in situ from the reaction of isoselenocyanate and L-amino esters, with α-bromoketones proceeded smoothly under ecofriendly conditions, i.e., at room temperature and under ultrasonication (Scheme 40) [88].
Chen et al. reported the construction of β-sulfonylvinylselane bond via the visible-light mediated MCR cascade of diselenides, alkynes, and SO2. In this reaction, novel class of β-sulfonylvinylselanes in high selectivity for E configuration and in moderate yields (up to 71%) (Scheme 41) [89].

2.3. Multicomponent Polymerization Synthesis of OSe Compounds

In 2018, Tuten et al. reported the multicomponent polymerization reaction of elemental Se, amines, and isocyanides to form polyselenoureas in one step and at room temperature using DCM as the solvent (Scheme 42) [90].
In 2019, Wu et al. reported the synthesis of functionalized and structurally diverse polyselenoureas via catalyst-free and solvent-free MC polymerizations of elemental Se, diisocyanides, and aliphatic/aromatic diamines. It is worth noting that the obtained polyselenoureas encompassed enhanced thermal stability and solubility, long-term stability, and the potential extraction of gold ions (Au3+) from mixed-metal ion solutions (Scheme 43) [91].
In 2021, the same group by Tang et al. reported the synthesis of alicyclic poly(oxaselenolane)s at room temperature via metal-free multicomponent polymerizations of elemental Se dipropargyl alcohols and diisocyanides. It is worth noting that poly(oxaselenolane)s were obtained in high yields (up to 93%), high Se contents (up to 33.7 wt %), high molecular weights (up to 15 600 g/mol), and high thermal and chemical stability as well as excellent light refractivity, good solubility, and processability. Furthermore, the polymerization reaction encompassed a broad scope of the diisocyanides (e.g., benzyl and aromatic) as well as various dipropargyl alcohols (Scheme 44) [92].

3. Conclusions

In conclusion, the direct one-pot multicomponent synthesis of OSe compounds has emerged as a potential and atom-economic strategy. Furthermore, different metal-free, as well as metal-catalyzed, reactions evolved during the last decade. These approaches open new scopes for synthesizing OSe compounds, a group of compounds with attractive chemical, biological, and physical activities. Without a doubt, novel and improved strategies for synthesizing OSe compounds will also be released soon, addressing challenges such as site-selectivity, late-stage selenylation of natural products, and complex molecules.

Author Contributions

Conceptualization, S.S. and I.Y.; methodology, S.S. and I.Y.; software, I.Y. and S.S.; validation, M.G., H.M.A.E.-L. and M.M.K.; formal analysis, S.S. and I.Y.; investigation, S.S. and I.Y.; resources, M.G., H.M.A.E.-L. and M.M.K.; data curation, S.S. and I.Y.; writing—original draft preparation, S.S. and I.Y.; writing—review and editing, S.S. and I.Y.; visualization, M.G., H.M.A.E.-L. and M.M.K.; supervision, S.S. and I.Y.; project administration, S.S.; funding acquisition, M.G., H.M.A.E.-L. and M.M.K. All authors have read and agreed to the published version of the manuscript.

Funding

This research was funded by King Faisal University, Al-Ahsa, Saudi Arabia, under the research group project track (Grant No. 1811004).

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

The data presented in this study are available on request from the corresponding author.

Acknowledgments

The authors acknowledge the Deanship of Scientific Research at King Faisal University, Saudi Arabia, for financial support under the research group project track (Grant No. 1811004).

Conflicts of Interest

The authors declare no conflict of interest.

References

  1. Kalimuthu, K.; Keerthana, C.K.; Mohan, M.; Arivalagan, J.; Christyraj, J.R.S.S.; Firer, M.A.; Choudry, M.H.A.; Anto, R.J.; Lee, Y.J. The emerging role of selenium metabolic pathways in cancer: New therapeutic targets for cancer. J. Cell. Biochem. 2022, 123, 532–542. [Google Scholar] [CrossRef] [PubMed]
  2. Phadnis, P.P. Synthesis Strategies for Organoselenium Compounds and Their Potential Applications in Human Life. In Handbook on Synthesis Strategies for Advanced Materials; Springer: Berlin/Heidelberg, Germany, 2021; pp. 537–641. [Google Scholar] [CrossRef]
  3. Radomska, D.; Czarnomysy, R.; Radomski, D.; Bielawska, A.; Bielawski, K. Selenium as a Bioactive Micronutrient in the Human Diet and Its Cancer Chemopreventive Activity. Nutrients 2021, 13, 1649. [Google Scholar] [CrossRef] [PubMed]
  4. Handy, D.E.; Joseph, J.; Loscalzo, J. Selenium, a Micronutrient that Modulates Cardiovascular Health via Redox Enzymology. Nutrients 2021, 13, 3238. [Google Scholar] [CrossRef] [PubMed]
  5. Schomburg, L. The other view: The trace element selenium as a micronutrient in thyroid disease, diabetes, and beyond. Hormones 2020, 19, 15–24. [Google Scholar] [CrossRef]
  6. Xu, J.; Gong, Y.; Sun, Y.; Cai, J.; Liu, Q.; Bao, J.; Yang, J.; Zhang, Z. Impact of Selenium Deficiency on Inflammation, Oxidative Stress, and Phagocytosis in Mouse Macrophages. Biol. Trace Elem. Res. 2020, 194, 237–243. [Google Scholar] [CrossRef]
  7. Li, B.; Li, W.; Tian, Y.; Guo, S.; Qian, L.; Xu, D.; Cao, N. Selenium-Alleviated Hepatocyte Necrosis and DNA Damage in Cyclophosphamide-Treated Geese by Mitigating Oxidative Stress. Biol. Trace Elem. Res. 2020, 193, 508–516. [Google Scholar] [CrossRef]
  8. Singh, F.V.; Wirth, T. Selenium reagents as catalysts. Catal. Sci. Technol. 2019, 9, 1073–1091. [Google Scholar] [CrossRef]
  9. Sanmartín, C.; Ruberte, A.C.; Ibáñez, E.; Moreno, E.; Espuelas, S.; Plano, D. Selenium Entities: Promising Scaffolds for the Treatment of Cancer and Leishmania. Curr. Org. Synth. 2017, 14, 1075–1081. [Google Scholar] [CrossRef]
  10. Bevinakoppamath, S.; Ahmed, A.M.S.; Ramachandra, S.C.; Vishwanath, P.; Prashant, A. Chemopreventive and Anticancer Property of Selenoproteins in Obese Breast Cancer. Front. Pharmacol. 2021, 12, 618172. [Google Scholar] [CrossRef]
  11. Nogueira, C.W.; Barbosa, N.V.; Rocha, J.B.T. Toxicology and pharmacology of synthetic organoselenium compounds: An update. Arch. Toxicol. 2021, 95, 1179–1226. [Google Scholar] [CrossRef]
  12. Shaaban, S.; Zarrouk, A.; Vervandier-Fasseur, D.; Al-Faiyz, Y.S.; El-Sawy, H.; Althagafi, I.; Andreoletti, P.; Cherkaoui-Malki, M. Cytoprotective organoselenium compounds for oligodendrocytes. Arab. J. Chem. 2021, 14, 103051. [Google Scholar] [CrossRef]
  13. Chen, Z.; Lai, H.; Hou, L.; Chen, T. Rational design and action mechanisms of chemically innovative organoselenium in cancer therapy. Chem. Commun. 2020, 56, 179–196. [Google Scholar] [CrossRef] [PubMed]
  14. Bartolini, D.; Sancineto, L.; de Bem, A.F.; Tew, K.D.; Santi, C.; Radi, R.; Toquato, P.; Galli, F. Selenocompounds in Cancer Therapy: An Overview. Adv. Cancer Res. 2017, 136, 259–302. [Google Scholar] [CrossRef] [PubMed]
  15. Zhu, E.; Fu, L.; Lu, Y.; Jiang, W.; Jee, M.H.; Liu, R.; Li, Z.; Che, G.; Woo, H.Y.; Liu, C. NIR-Absorbing Electron Acceptor Based on a Selenium-Heterocyclic Core Attaching to Phenylalkyl Side Chains for Polymer Solar Cells with 17.3% Efficiency. ACS Appl. Mater. Interfaces 2022, 14, 7082–7092. [Google Scholar] [CrossRef]
  16. Fu, Y.; Sun, Y.; Tang, H.; Wang, L.; Yu, H.; Cao, D. Selenium-containing D-A-D-type dopant-free hole transport materials for perovskite solar cells. Dye. Pigment. 2021, 191, 109339. [Google Scholar] [CrossRef]
  17. Thomas, J.; Dong, Z.; Dehaen, W.; Smet, M. Selenium/Tellurium-Containing Hyperbranched Polymers: Effect of Molecular Weight and Degree of Branching on Glutathione Peroxidase-Like Activity. Macromol. Rapid Commun. 2012, 33, 2127–2132. [Google Scholar] [CrossRef]
  18. Pons, D.G.; Moran, C.; Alorda-Clara, M.; Oliver, J.; Roca, P.; Sastre-Serra, J. Micronutrients Selenomethionine and Selenocysteine Modulate the Redox Status of MCF-7 Breast Cancer Cells. Nutrients 2020, 12, 865. [Google Scholar] [CrossRef] [Green Version]
  19. Cardoso, B.R.; Roberts, B.R.; Bush, A.I.; Hare, D.J. Selenium, selenoproteins and neurodegenerative diseases. Metallomics 2015, 7, 1213–1228. [Google Scholar] [CrossRef] [Green Version]
  20. Metanis, N.; Hilvert, D. Natural and synthetic selenoproteins. Curr. Opin. Chem. Biol. 2014, 22, 27–34. [Google Scholar] [CrossRef]
  21. Benelli, J.L.; Poester, V.R.; Munhoz, L.S.; Melo, A.M.; Trápaga, M.R.; Stevens, D.A.; Xavier, M.O. Ebselen and diphenyl diselenide against fungal pathogens: A systematic review. Med. Mycol. 2021, 59, 409–421. [Google Scholar] [CrossRef]
  22. Weglarz-Tomczak, E.; Tomczak, J.M.; Talma, M.; Brul, S. Ebselen as a highly active inhibitor of PLProCoV2. bioRxiv 2020. [Google Scholar] [CrossRef]
  23. Wang, L.; Yang, Z.; Fu, J.; Yin, H.; Xiong, K.; Tan, Q.; Jin, H.; Li, J.; Wang, T.; Tang, W.; et al. Ethaselen: A potent mammalian thioredoxin reductase 1 inhibitor and novel organoselenium anticancer agent. Free Radic. Biol. Med. 2012, 52, 898–908. [Google Scholar] [CrossRef] [PubMed]
  24. Shaaban, S.; Ashmawy, A.M.; Negm, A.; Wessjohann, L.A. Synthesis and biochemical studies of novel organic selenides with increased selectivity for hepatocellular carcinoma and breast adenocarcinoma. Eur. J. Med. Chem. 2019, 179, 515–526. [Google Scholar] [CrossRef] [PubMed]
  25. Shaaban, S.; Vervandier-Fasseur, D.; Andreoletti, P.; Zarrouk, A.; Richard, P.; Negm, A.; Manolikakes, G.; Jacob, C.; Cherkaoui-Malki, M. Cytoprotective and antioxidant properties of organic selenides for the myelin-forming cells, oligodendrocytes. Bioorganic Chem. 2018, 80, 43–56. [Google Scholar] [CrossRef] [PubMed]
  26. Shaaban, S.; Negm, A.; Sobh, M.A.; Wessjohann, L.A. Organoselenocyanates and symmetrical diselenides redox modulators: Design, synthesis and biological evaluation. Eur. J. Med. Chem. 2015, 97, 190–201. [Google Scholar] [CrossRef] [PubMed]
  27. Yao, Q.; Kinney, A.E.P.; Zheng, C. Selenium-Ligated Palladium (II) Complexes as Highly Active Catalysts for Carbon−Carbon Coupling Reactions: The Heck Reaction. Org. Lett. 2004, 6, 2997–2999. [Google Scholar] [CrossRef] [PubMed]
  28. Shaaban, S.; Diestel, R.; Hinkelmann, B.; Muthukumar, Y.; Verma, R.P.; Sasse, F.; Jacob, C. Novel peptidomimetic compounds containing redox active chalcogens and quinones as potential anticancer agents. Eur. J. Med. Chem. 2012, 58, 192–205. [Google Scholar] [CrossRef]
  29. Shaaban, S.; Arafat, M.A.; Gaffer, H.E.; Hamama, W.S. Synthesis and anti-tumor evaluation of novel organoselenocyanates and symmetrical diselenides dyestuffs. Pharma Chem. 2014, 6, 186–193. [Google Scholar]
  30. El-Lateef, H.M.A.; Shaaban, S.; Khalaf, M.M.; Toghan, A.; Shalabi, K. Synthesis, experimental, and computational studies of water soluble anthranilic organoselenium compounds as safe corrosion inhibitors for J55 pipeline steel in acidic oilfield formation water. Colloids Surfaces A Physicochem. Eng. Asp. 2021, 625, 126894. [Google Scholar] [CrossRef]
  31. Ma, Y.T.; Liu, M.C.; Zhou, Y.B.; Wu, H.Y. Synthesis of Organoselenium Compounds with Elemental Selenium. Adv. Synth. Catal. 2021, 363, 5386–5406. [Google Scholar] [CrossRef]
  32. Zhao, X.; Liao, L. Modern Organoselenium Catalysis: Opportunities and Challenges. Synlett 2021, 32, 1262–1268. [Google Scholar] [CrossRef]
  33. Lenardão, E.J.; Santi, C.; Sancineto, L. New Frontiers in Organoselenium Compounds; Springer: Berlin/Heidelberg, Germany, 2018. [Google Scholar]
  34. Jain, V.K.; Priyadarsini, K.I. Organoselenium Compounds in Biology and Medicine; The Royalty Society of Chemistry: London, UK, 2017. [Google Scholar]
  35. Shaaban, S.; Arafat, M.A.; Hamama, W.S. Vistas in the domain of organo selenocyanates. Arkivoc 2014, i, 470–505. [Google Scholar] [CrossRef] [Green Version]
  36. Khan, T.; Ahmad, R.; Azad, I.; Raza, S.; Joshi, S.; Khan, A.R. Computer-aided drug design and virtual screening of targeted combinatorial libraries of mixed-ligand transition metal complexes of 2-butanone thiosemicarbazone. Comput. Biol. Chem. 2018, 75, 178–195. [Google Scholar] [CrossRef] [PubMed]
  37. Shaaban, S.; Abdel-Wahab, B.F. Groebke-Blackburn-Bienaymé multicomponent reaction: Emerging chemistry for drug discovery. Mol. Divers. 2016, 20, 233–254. [Google Scholar] [CrossRef]
  38. Wang, S.-L.; Zhang, G.; Jie, D.; Jiang, B.; Wang, X.-H.; Tu, S.-J. Microwave-Assisted Multicomponent Reactions: Rapid and Regioselective Formation of New Extended Angular Fused Aza-Heterocycles. Comb. Chem. High Throughput Screen. 2012, 15, 400–410. [Google Scholar] [CrossRef]
  39. Dömling, A.; Beck, B.; Fuchs, T.; Yazbak, A. Parallel Synthesis of Arrays of Amino-Acid-Derived Isocyanoamides Useful as Starting Materials in IMCR. J. Comb. Chem. 2006, 8, 872–880. [Google Scholar] [CrossRef]
  40. Ulaczyk-Lesanko, A.; Hall, D.G. Wanted: New multicomponent reactions for generating libraries of polycyclic natural products. Curr. Opin. Chem. Biol. 2005, 9, 266–276. [Google Scholar] [CrossRef]
  41. Pirrung, M.C.; Das Sarma, K. Multicomponent Reactions Are Accelerated in Water. J. Am. Chem. Soc. 2004, 126, 444–445. [Google Scholar] [CrossRef]
  42. Kolb, J.; Beck, B.; Almstetter, M.; Heck, S.; Herdtweck, E.; Domling, A. New MCRs: The first 4-component reaction leading to 2,4-disubstituted thiazoles. Mol. Divers. 2003, 6, 297–313. [Google Scholar] [CrossRef]
  43. Ugi, I.; Heck, S. The multicomponent reactions and their libraries for natural and preparative chemistry. Comb. Chem. High Throughput Screen. 2001, 4, 1–34. [Google Scholar] [CrossRef]
  44. Burchak, O.N.; Mugherli, L.; Ostuni, M.; Lacapère, J.J.; Balakirev, M.Y. Combinatorial Discovery of Fluorescent Pharmacophores by Multicomponent Reactions in Droplet Arrays. J. Am. Chem. Soc. 2011, 133, 10058–10061. [Google Scholar] [CrossRef] [PubMed]
  45. Domling, A. The discovery of new isocyanide-based multi-component reactions. Curr. Opin. Chem. Biol. 2000, 4, 318–323. [Google Scholar] [CrossRef]
  46. Suay-García, B.; Bueso-Bordils, J.I.; Falcó, A.; Antón-Fos, G.M.; Alemán-López, P.A. Virtual Combinatorial Chemistry and Pharmacological Screening: A Short Guide to Drug Design. Int. J. Mol. Sci. 2022, 23, 1620. [Google Scholar] [CrossRef] [PubMed]
  47. Kennedy, J.P.; Williams, L.; Bridges, T.M.; Daniels, R.N.; Weaver, D.; Lindsley, C.W. Application of Combinatorial Chemistry Science on Modern Drug Discovery. J. Comb. Chem. 2008, 10, 345–354. [Google Scholar] [CrossRef]
  48. Semreen, M.H.; El-Awady, R.; Abu-Odeh, R.A.; Saber-Ayad, M.; Al-Qawasmeh, R.; Chouaib, S.; Voelter, W.; Al-Tel, T.H. Tandem Multicomponent Reactions Toward the Design and Synthesis of Novel Antibacterial and Cytotoxic Motifs. Curr. Med. Chem. 2013, 20, 1445–1459. [Google Scholar] [CrossRef]
  49. Chéron, N.; Ramozzi, R.; El Kaïm, L.; Grimaud, L.; Fleurat-Lessard, P. Challenging 50 Years of Established Views on Ugi Reaction: A Theoretical Approach. J. Org. Chem. 2012, 77, 1361–1366. [Google Scholar] [CrossRef]
  50. Gulevich, A.V.; Zhdanko, A.G.; Orru, R.V.A.; Nenajdenko, V.G. Synthetic Application of Isocyanoacetic Acid Derivatives. In Isocyanide Chemistry; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2012; pp. 109–158. [Google Scholar]
  51. de Oliveira, I.M.; Pimenta, D.C.; Zukerman-Schpector, J.; Stefani, H.A.; Manarin, F. Copper(i)/succinic acid cooperatively catalyzed one-pot synthesis of organoselenium-propargylamines via A3-coupling. New J. Chem. 2018, 42, 10118–10123. [Google Scholar] [CrossRef]
  52. Liu, H.; Fang, Y.; Yin, L.; Wang, S.-Y.; Ji, S.-J. Copper(I)-Catalyzed Ligand-Promoted Multicomponent Reactions of Isocyanides, Selenium, Amines, and Iodoarenes: Access to Highly Functionalized Carbamimidoselenoates. J. Org. Chem. 2017, 82, 10866–10874. [Google Scholar] [CrossRef]
  53. Aquino, T.B.; do Nascimento, J.E.R.; Dias, Í.F.C.; de Oliveira, D.H.; Barcellos, T.; Lenardão, E.J.; Perin, G.; Alves, D.; Jacob, R.G. Synthesis of (arylselanyl)- and (arylsulfenyl)-alkyl-1,2,3-triazolo-1,3,6-triazonines via a copper-catalyzed multicomponent reaction. Tetrahedron Lett. 2018, 59, 1080–1083. [Google Scholar] [CrossRef]
  54. Zhang, L.-L.; Li, Y.-T.; Gao, T.; Guo, S.-S.; Yang, B.; Meng, Z.-H.; Dai, Q.-P.; Xu, Z.-B.; Wu, Q.-P. Efficient Synthesis of Diverse 5-Thio- or 5-Selenotriazoles: One-Pot Multicomponent Reaction from Elemental Sulfur or Selenium. Synthesis 2019, 51, 4170–4182. [Google Scholar] [CrossRef] [Green Version]
  55. Gao, X.; Tang, L.; Huang, L.; Huang, Z.-S.; Ma, Y.; Wu, G. Oxidative Aminoarylselenation of Maleimides via Copper-Catalyzed Four-Component Cross-Coupling. Org. Lett. 2019, 21, 745–748. [Google Scholar] [CrossRef] [PubMed]
  56. Begini, F.; Balaguez, R.A.; Larroza, A.; Lopes, E.F.; Lenardão, E.J.; Santi, C.; Alves, D. Synthesis of 4-Arylselanyl-1H-1,2,3-triazoles from Selenium-Containing Carbinols. Molecules 2021, 26, 2224. [Google Scholar] [CrossRef] [PubMed]
  57. Rather, R.A.; Ara, T. Copper catalyzed synthesis of 3-((arylethynyl)selanyl)-1H-indoles via selenium insertion reaction by using elemental selenium. Tetrahedron 2021, 96, 132386. [Google Scholar] [CrossRef]
  58. Lara, R.G.; Rosa, P.C.; Soares, L.K.; Silva, M.S.; Jacob, R.G.; Perin, G. A simple and stereoselective synthesis of (Z)-1,2-bis-arylselanyl alkenes from alkynes using KF/Al2O3. Tetrahedron 2012, 68, 10414–10418. [Google Scholar] [CrossRef]
  59. de Oliveira, I.M.; Vasconcelos, S.S.N.; Barbeiro, C.S.; Correra, T.C.; Shamim, A.; Pimenta, D.C.; Caracelli, I.; Zukerman-Schpector, J.; Stefani, H.A.; Manarin, F. Ytterbium(iii)-catalyzed three-component reactions: Synthesis of 4-organoselenium-quinolines. New J. Chem. 2017, 41, 9884–9888. [Google Scholar] [CrossRef]
  60. Sakai, N.; Horikawa, S.; Ogiwara, Y. Indium-Catalyzed Direct Conversion of Lactones into Thiolactones and Selenolactones in the Presence of Elemental Sulfur and Selenium. Synthesis 2017, 50, 565–574. [Google Scholar] [CrossRef]
  61. Attia, Y.A.; Abdel-Hafez, S.H. Reusable photoresponsive Ag/AgCl nanocube-catalyzed one-pot synthesis of seleno[2,3-b]pyridine derivatives. Res. Chem. Intermed. 2020, 46, 3165–3177. [Google Scholar] [CrossRef]
  62. Attia, Y.A.; Abdel-Hafez, S.H. Nano-Co3O4-catalyzed microwave-assisted one-pot synthesis of some seleno [2,3-b] pyridine/quinoline derivatives. Res. Chem. Intermed. 2021, 47, 3719–3732. [Google Scholar] [CrossRef]
  63. Trofimov, B.; Artem’Ev, A.; Gusarova, N.; Malysheva, S.; Kraikivskii, P.; Belogorlova, N. Efficient General Synthesis of Alkylammonium Diselenophosphinates via Multicomponent One-Pot Reaction of Secondary Phosphines with Elemental Selenium and Amines. Synthesis 2010, 2010, 3724–3730. [Google Scholar] [CrossRef]
  64. Artem’Ev, A.V.; Gusarova, N.K.; Malysheva, S.F.; Trofimov, B.A. Three-component reaction of secondary phosphines with elemental selenium and amines. Russ. J. Org. Chem. 2010, 46, 592–593. [Google Scholar] [CrossRef]
  65. Artem’Ev, A.V.; Gusarova, N.K.; Malysheva, S.F.; Mamatyuk, V.I.; Gatilov, Y.V.; Ushakov, I.A.; Trofimov, B.A. One-Pot Atom-Economic Synthesis of Thioselenophosphinates via a New Multicomponent Reaction of Secondary Phosphanes with Elemental Sulfur, Selenium, and Amines. Eur. J. Org. Chem. 2010, 2010, 6157–6160. [Google Scholar] [CrossRef]
  66. Artem’Ev, A.V.; Gusarova, N.K.; Malysheva, S.F.; Gatilov, Y.V.; Mamatyuk, V.I. Efficient Synthesis of Lupininium, Anabasinium and Quininium Thioselenophosphinates via a Multi-component Reaction between Secondary Phosphines, Sulfur, Selenium and Alkaloids. Org. Prep. Proced. Int. 2012, 44, 262–270. [Google Scholar] [CrossRef]
  67. de la Torre, A.F.; Ali, A.; Galetto, F.Z.; Braga, A.L.; Delgado, J.A.C.; Paixão, M.W. One-pot organocatalytic/multicomponent approach for the preparation of novel enantioenriched non-natural selenium-based peptoids and peptide–peptoid conjugates. Mol. Divers. 2020, 24, 1–10. [Google Scholar] [CrossRef] [PubMed]
  68. Singh, S.; Mosslemin, M.H.; Hassanabadi, A. Synthesis of 5-Aryl-1,3-Dimethyl-7-Selenoxopyrimidino [4,5-d] Pyrimidine-2,4 (1H,3H)-Dione. J. Chem. Res. 2018, 42, 264–266. [Google Scholar] [CrossRef]
  69. Liu, H.; Fang, Y.; Wang, S.-Y.; Ji, S.-J. TEMPO-Catalyzed Aerobic Oxidative Selenium Insertion Reaction: Synthesis of 3-Selenylindole Derivatives by Multicomponent Reaction of Isocyanides, Selenium Powder, Amines, and Indoles under Transition-Metal-Free Conditions. Org. Lett. 2018, 20, 930–933. [Google Scholar] [CrossRef]
  70. Liu, H.-W.; Fang, Y.; Wang, S.-Y.; Ji, S.-J. Base-Promoted Multicomponent Reactions: A Synthesis of 2-Amino-1,3-selenazole Derivatives. J. Org. Chem. 2020, 85, 3508–3516. [Google Scholar] [CrossRef]
  71. Zhao, Z.; Zhang, Y.; Shao, Y.; Xiong, W.; Li, R.; Chen, J. Synthesis of 3-Selenylindoles through Organoselenium-Promoted Selenocyclization of 2-Vinylaniline. J. Org. Chem. 2020, 85, 15015–15025. [Google Scholar] [CrossRef]
  72. Liu, H.; Cai, Z.-J.; Ji, S.-J. Access to 3-alkylselenindoles by multicomponent reaction of indoles, selenium powder and unactivated alkyl halides under transition-metal-free conditions (in press). Chin. Chem. Lett. 2022. [Google Scholar] [CrossRef]
  73. Li, L.; Peng, X.; Lu, J.-M.; Jiang, X. One-pot four-component assembly for diselenocarbamates. Org. Chem. Front. 2021, 8, 6642–6647. [Google Scholar] [CrossRef]
  74. Fang, Y.; Wang, S.-Y.; Shen, X.-B.; Ji, S.-J. Base-promoted cascade reaction of isocyanides, selenium and amines: A practical approach to 2-aminobenzo[d][1,3]selenazines under metal-free conditions. Org. Chem. Front. 2015, 2, 1338–1341. [Google Scholar] [CrossRef]
  75. Fang, Y.; Zhu, Z.-L.; Xu, P.; Wang, S.-Y.; Ji, S.-J. Aerobic radical-cascade cycloaddition of isocyanides, selenium and imidamides: Facile access to 1,2,4-selenadiazoles under metal-free conditions. Green Chem. 2017, 19, 1613–1618. [Google Scholar] [CrossRef]
  76. Heredia, A.A.; Peñéñory, A.B. Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions. Beilstein J. Org. Chem. 2017, 13, 910–918. [Google Scholar] [CrossRef] [PubMed] [Green Version]
  77. Prabhu, C.P.; Phadnis, P.P.; Wadawale, A.; Priyadarsini, K.I.; Jain, V.K. One-pot synthesis of phenylseleno N-acetyl α-amino acids: Supra-molecular self-assembling in organoselenium compounds. J. Organomet. Chem. 2013, 745–746, 140–147. [Google Scholar] [CrossRef]
  78. Armstrong, A.; Emmerson, D.P.G. Enantioselective Synthesis of α-Alkyl, α-Vinyl Amino Acids via [2,3]-Sigmatropic Rearrangement of Selenimides. Org. Lett. 2011, 13, 1040–1043. [Google Scholar] [CrossRef] [PubMed]
  79. Pan, X.; Zhu, J.; Zou, J.; Zhang, Z.; Cheng, Z.; Zhou, N.; Zhang, W.; Zhu, X. Straightforward and Highly Efficient Synthesis of Diselenocarbamates. Org. Lett. 2012, 14, 6170–6173. [Google Scholar] [CrossRef]
  80. Ahn, H.R.; Cho, Y.A.; Kim, D.-S.; Chin, J.; Gyoung, Y.-S.; Lee, S.; Kang, H.; Ham, J. A Facile One-Pot Preparation of Organoselanyltrifluoroborates from Dihalobenzenes and Their Cross-Coupling Reaction. Org. Lett. 2009, 11, 361–364. [Google Scholar] [CrossRef]
  81. Sands, K.N.; Gelfand, B.S.; Back, T.G. One-Pot Synthesis of Aryl Selenonic Acids and Some Unexpected Byproducts. J. Org. Chem. 2021, 86, 9938–9944. [Google Scholar] [CrossRef]
  82. Li, L.; Wu, J.; Wei, L.; Lu, J.; Jiang, X. One-Pot Four-Component Assembling for Selenoureas. J. Org. Chem. 2021, 86, 446–454. [Google Scholar] [CrossRef]
  83. El-Senduny, F.F.; Shabana, S.M.; Rösel, D.; Brabek, J.; Althagafi, I.; Angeloni, G.; Manolikakes, G.; Shaaban, S. Urea-functionalized organoselenium compounds as promising anti-HepG2 and apoptosis-inducing agents. Future Med. Chem. 2021, 13, 1655–1677. [Google Scholar] [CrossRef]
  84. Shaaban, S.; Negm, A.; Ashmawy, A.M.; Ahmed, D.; Wessjohann, L.A. Combinatorial synthesis, in silico, molecular and biochemical studies of tetrazole-derived organic selenides with increased selectivity against hepatocellular carcinoma. Eur. J. Med. Chem. 2016, 122, 55–71. [Google Scholar] [CrossRef]
  85. Shaaban, S.; Sasse, F.; Burkholz, T.; Jacob, C. Sulfur, selenium and tellurium pseudopeptides: Synthesis and biological evaluation. Bioorganic Med. Chem. 2014, 22, 3610–3619. [Google Scholar] [CrossRef] [PubMed]
  86. Shaaban, S.; Negm, A.; Sobh, M.A.; Wessjohann, L.A. Expeditious Entry to Functionalized Pseudo-peptidic Organoselenide Redox Modulators via Sequential Ugi/SN Methodology. AntiCancer Agents Med. Chem. 2016, 16, 621–632. [Google Scholar] [CrossRef] [PubMed]
  87. Shaaban, S.; Shabana, S.M.; Al-Faiyz, Y.S.; Manolikakes, G.; El-Senduny, F.F. Enhancing the chemosensitivity of HepG2 cells towards cisplatin by organoselenium pseudopeptides. Bioorg. Chem. 2021, 109, 104713. [Google Scholar] [CrossRef] [PubMed]
  88. Chang, W.-J.; Kulkarni, M.V.; Sun, C.-M. Regioselective one-pot three component synthesis of chiral 2-iminoselenazolines under sonication. RSC Adv. 2015, 5, 97113–97120. [Google Scholar] [CrossRef]
  89. Chen, H.; Ding, R.; Tang, H.; Pan, Y.; Xu, Y.; Chen, Y. Simultaneous Construction of C−Se and C−S Bonds via the Visible-Light-Mediated Multicomponent Cascade Reaction of Diselenides, Alkynes, and SO2. Chem.-Asian J. 2019, 14, 3264–3268. [Google Scholar] [CrossRef]
  90. Tuten, B.T.; Bloesser, F.R.; Marshall, D.L.; Michalek, L.; Schmitt, C.W.; Blanksby, S.J.; Barner-Kowollik, C. Polyselenoureas via Multicomponent Polymerizations Using Elemental Selenium as Monomer. ACS Macro Lett. 2018, 7, 898–903. [Google Scholar] [CrossRef]
  91. Wu, X.; Lin, H.; Dai, F.; Hu, R.; Tang, B.Z. Functional Polyselenoureas for Selective Gold Recovery Prepared from Catalyst-Free Multicomponent Polymerizations of Elemental Selenium. CCS Chem. 2020, 2, 191–202. [Google Scholar] [CrossRef]
  92. Wu, X.; He, J.; Hu, R.; Tang, B.Z. Room-Temperature Metal-Free Multicomponent Polymerizations of Elemental Selenium toward Stable Alicyclic Poly(oxaselenolane)s with High Refractive Index. J. Am. Chem. Soc. 2021, 143, 15723–15731. [Google Scholar] [CrossRef]
Polymers 14 02208 g001 550
Figure 1. Organoselenium compounds (I–VI) with potential biological activities and diverse applications.
Figure 1. Organoselenium compounds (I–VI) with potential biological activities and diverse applications.
Polymers 14 02208 g001
Polymers 14 02208 sch001 550
Scheme 1. Synthesis of OSe propargylamines.
Scheme 1. Synthesis of OSe propargylamines.
Polymers 14 02208 sch001
Polymers 14 02208 sch002 550
Scheme 2. Synthesis of functionalized isoselenoureas.
Scheme 2. Synthesis of functionalized isoselenoureas.
Polymers 14 02208 sch002
Polymers 14 02208 sch003 550
Scheme 3. Synthesis of (arylselanyl)-alkyl-1,2,3-triazolo-1,3,6-triazonines.
Scheme 3. Synthesis of (arylselanyl)-alkyl-1,2,3-triazolo-1,3,6-triazonines.
Polymers 14 02208 sch003
Polymers 14 02208 sch004 550
Scheme 4. Synthesis of 5-selenotriazoles.
Scheme 4. Synthesis of 5-selenotriazoles.
Polymers 14 02208 sch004
Polymers 14 02208 sch005 550
Scheme 5. Aminoarylselenation of maleimides.
Scheme 5. Aminoarylselenation of maleimides.
Polymers 14 02208 sch005
Polymers 14 02208 sch006 550
Scheme 6. Synthesis of 4-arylselanyl-1H-1,2,3-triazoles.
Scheme 6. Synthesis of 4-arylselanyl-1H-1,2,3-triazoles.
Polymers 14 02208 sch006
Polymers 14 02208 sch007 550
Scheme 7. Synthesis of 3-((arylethynyl)selanyl)-1H-indoles.
Scheme 7. Synthesis of 3-((arylethynyl)selanyl)-1H-indoles.
Polymers 14 02208 sch007
Polymers 14 02208 sch008 550
Scheme 8. Synthesis of (Z)-1,2-bis-arylselanyl alkenes.
Scheme 8. Synthesis of (Z)-1,2-bis-arylselanyl alkenes.
Polymers 14 02208 sch008
Polymers 14 02208 sch009 550
Scheme 9. Synthesis of 2,4- disubstituted Se-quinoline derivatives.
Scheme 9. Synthesis of 2,4- disubstituted Se-quinoline derivatives.
Polymers 14 02208 sch009
Polymers 14 02208 sch010 550
Scheme 10. Synthesis of selenolactones.
Scheme 10. Synthesis of selenolactones.
Polymers 14 02208 sch010
Polymers 14 02208 sch011 550
Scheme 11. Synthesis of seleno [2,3-b]pyridine derivatives.
Scheme 11. Synthesis of seleno [2,3-b]pyridine derivatives.
Polymers 14 02208 sch011
Polymers 14 02208 sch012 550
Scheme 12. Synthesis of selenopyridine and quinoline derivatives.
Scheme 12. Synthesis of selenopyridine and quinoline derivatives.
Polymers 14 02208 sch012
Polymers 14 02208 sch013 550
Scheme 13. Synthesis of alkylammonium diselenophosphinates.
Scheme 13. Synthesis of alkylammonium diselenophosphinates.
Polymers 14 02208 sch013
Polymers 14 02208 sch014 550
Scheme 14. Synthesis of diselenophosphinates.
Scheme 14. Synthesis of diselenophosphinates.
Polymers 14 02208 sch014
Polymers 14 02208 sch015 550
Scheme 15. Synthesis of mono-, di-, and trialkylammonium thioselenophosphinates.
Scheme 15. Synthesis of mono-, di-, and trialkylammonium thioselenophosphinates.
Polymers 14 02208 sch015
Polymers 14 02208 sch016 550
Scheme 16. Synthesis of mono-, di-, and trialkylammonium thioselenophosphinates of lupinine, anabasine, and quinine.
Scheme 16. Synthesis of mono-, di-, and trialkylammonium thioselenophosphinates of lupinine, anabasine, and quinine.
Polymers 14 02208 sch016
Polymers 14 02208 sch017 550
Scheme 17. Synthesis of selenocysteine-based peptoids and peptide–peptoid conjugates.
Scheme 17. Synthesis of selenocysteine-based peptoids and peptide–peptoid conjugates.
Polymers 14 02208 sch017
Polymers 14 02208 sch018 550
Scheme 18. Synthesis of 5-aryl-1,3-dimethyl-7-selenoxopyrimidino [4,5-d]pyrimidine-2,4(1H,3H)-diones.
Scheme 18. Synthesis of 5-aryl-1,3-dimethyl-7-selenoxopyrimidino [4,5-d]pyrimidine-2,4(1H,3H)-diones.
Polymers 14 02208 sch018
Polymers 14 02208 sch019 550
Scheme 19. Synthesis of Se functionalization of indoles.
Scheme 19. Synthesis of Se functionalization of indoles.
Polymers 14 02208 sch019
Polymers 14 02208 sch020 550
Scheme 20. Synthesis of 2-amino-1,3-selenazoles.
Scheme 20. Synthesis of 2-amino-1,3-selenazoles.
Polymers 14 02208 sch020
Polymers 14 02208 sch021 550
Scheme 21. Synthesis of 3-selenylindoles.
Scheme 21. Synthesis of 3-selenylindoles.
Polymers 14 02208 sch021
Polymers 14 02208 sch022 550
Scheme 22. Synthesis of 3-alkylselenindole derivatives.
Scheme 22. Synthesis of 3-alkylselenindole derivatives.
Polymers 14 02208 sch022
Polymers 14 02208 sch023 550
Scheme 23. Synthesis of diselenocarbamates.
Scheme 23. Synthesis of diselenocarbamates.
Polymers 14 02208 sch023
Polymers 14 02208 sch024 550
Scheme 24. Synthesis of 2-aminobenzo[d][1,3]selenazines.
Scheme 24. Synthesis of 2-aminobenzo[d][1,3]selenazines.
Polymers 14 02208 sch024
Polymers 14 02208 sch025 550
Scheme 25. Preparation of 1,2,4-selenadiazol-5-amine derivatives.
Scheme 25. Preparation of 1,2,4-selenadiazol-5-amine derivatives.
Polymers 14 02208 sch025
Polymers 14 02208 sch026 550
Scheme 26. Synthesized alkynyl selenides.
Scheme 26. Synthesized alkynyl selenides.
Polymers 14 02208 sch026
Polymers 14 02208 sch027 550
Scheme 27. Synthesis of phenylseleno N-acetyl amino acids.
Scheme 27. Synthesis of phenylseleno N-acetyl amino acids.
Polymers 14 02208 sch027
Polymers 14 02208 sch028 550
Scheme 28. Synthesis of trisubstituted allylic selenides.
Scheme 28. Synthesis of trisubstituted allylic selenides.
Polymers 14 02208 sch028
Polymers 14 02208 sch029 550
Scheme 29. Synthesis of diselenocarbamates.
Scheme 29. Synthesis of diselenocarbamates.
Polymers 14 02208 sch029
Polymers 14 02208 sch030 550
Scheme 30. Synthesis of diselenocarbamates.
Scheme 30. Synthesis of diselenocarbamates.
Polymers 14 02208 sch030
Polymers 14 02208 sch031 550
Scheme 31. Preparation of organoselanyltrifluoroborates.
Scheme 31. Preparation of organoselanyltrifluoroborates.
Polymers 14 02208 sch031
Polymers 14 02208 sch032 550
Scheme 32. Synthesis of structurally diverse selenonic acids.
Scheme 32. Synthesis of structurally diverse selenonic acids.
Polymers 14 02208 sch032
Polymers 14 02208 sch033 550
Scheme 33. Synthesis of unsymmetrical selenoureas and cycloselenoureas.
Scheme 33. Synthesis of unsymmetrical selenoureas and cycloselenoureas.
Polymers 14 02208 sch033
Polymers 14 02208 sch034 550
Scheme 34. Synthesis of urea-based selenocyanates and symmetrical diselenides.
Scheme 34. Synthesis of urea-based selenocyanates and symmetrical diselenides.
Polymers 14 02208 sch034
Polymers 14 02208 sch035 550
Scheme 35. Synthesis of peptide-like and tetrazole-based redox-active multifunctional OSe compounds.
Scheme 35. Synthesis of peptide-like and tetrazole-based redox-active multifunctional OSe compounds.
Polymers 14 02208 sch035
Polymers 14 02208 sch036 550
Scheme 36. Synthesis of tetrazole-based symmetrical diselenides and selenoquinones compounds.
Scheme 36. Synthesis of tetrazole-based symmetrical diselenides and selenoquinones compounds.
Polymers 14 02208 sch036
Polymers 14 02208 sch037 550
Scheme 37. Synthesis of different Se peptidomimetic compounds.
Scheme 37. Synthesis of different Se peptidomimetic compounds.
Polymers 14 02208 sch037
Polymers 14 02208 sch038 550
Scheme 38. Synthesis of symmetrical diselenide.
Scheme 38. Synthesis of symmetrical diselenide.
Polymers 14 02208 sch038
Polymers 14 02208 sch039 550
Scheme 39. The synthesis of new selenocyanate isocyanide and diselenide diisonitrile and explored their reactivities in Passerini, Ugi, and Azido-Ugi reactions.
Scheme 39. The synthesis of new selenocyanate isocyanide and diselenide diisonitrile and explored their reactivities in Passerini, Ugi, and Azido-Ugi reactions.
Polymers 14 02208 sch039
Polymers 14 02208 sch040 550
Scheme 40. Synthesis of chiral 2-iminoselenazolines.
Scheme 40. Synthesis of chiral 2-iminoselenazolines.
Polymers 14 02208 sch040
Polymers 14 02208 sch041 550
Scheme 41. Synthesis of β-sulfonylvinylselanes.
Scheme 41. Synthesis of β-sulfonylvinylselanes.
Polymers 14 02208 sch041
Polymers 14 02208 sch042 550
Scheme 42. The multicomponent polymerization synthesis of polyselenoureas.
Scheme 42. The multicomponent polymerization synthesis of polyselenoureas.
Polymers 14 02208 sch042
Polymers 14 02208 sch043 550
Scheme 43. Synthesis of functionalized and structurally diverse polyselenoureas.
Scheme 43. Synthesis of functionalized and structurally diverse polyselenoureas.
Polymers 14 02208 sch043
Polymers 14 02208 sch044 550
Scheme 44. Synthesis of alicyclic poly(oxaselenolane)s.
Scheme 44. Synthesis of alicyclic poly(oxaselenolane)s.
Polymers 14 02208 sch044
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Shaaban, S.; El-Lateef, H.M.A.; Khalaf, M.M.; Gouda, M.; Youssef, I. One-Pot Multicomponent Polymerization, Metal-, and Non-Metal-Catalyzed Synthesis of Organoselenium Compounds. Polymers 2022, 14, 2208. https://doi.org/10.3390/polym14112208

AMA Style

Shaaban S, El-Lateef HMA, Khalaf MM, Gouda M, Youssef I. One-Pot Multicomponent Polymerization, Metal-, and Non-Metal-Catalyzed Synthesis of Organoselenium Compounds. Polymers. 2022; 14(11):2208. https://doi.org/10.3390/polym14112208

Chicago/Turabian Style

Shaaban, Saad, Hany M. Abd El-Lateef, Mai M. Khalaf, Mohamed Gouda, and Ibrahim Youssef. 2022. "One-Pot Multicomponent Polymerization, Metal-, and Non-Metal-Catalyzed Synthesis of Organoselenium Compounds" Polymers 14, no. 11: 2208. https://doi.org/10.3390/polym14112208

APA Style

Shaaban, S., El-Lateef, H. M. A., Khalaf, M. M., Gouda, M., & Youssef, I. (2022). One-Pot Multicomponent Polymerization, Metal-, and Non-Metal-Catalyzed Synthesis of Organoselenium Compounds. Polymers, 14(11), 2208. https://doi.org/10.3390/polym14112208

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