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Organic Synthesis via Transition Metal-Catalysis
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Organic Synthesis via Transition Metal-Catalysis

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (31 December 2021) | Viewed by 30261

Printed Edition Available!
A printed edition of this Special Issue is available here.

Special Issue Editor

Prof. Dr. Bartolo Gabriele

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Guest Editor
Laboratory of Industrial and Synthetic Organic Chemistry (LISOC), Department of Chemistry and Chemical Technologies, University of Calabria, Via Pietro Bucci, 12/C, 87036 Arcavacata di Rende, Italy
Interests: new syntheses of high value added molecules through catalytic assembly of simple units; innovative syntheses of heterocyclic molecules of pharmaceutical; agrochemical; applicative interest; carbonylation chemistry; use of non-conventional solvents in organic synthesis; synthesis and semi-synthesis of bioactive compounds of pharmaceutical or agrochemical interest; synthesis of new materials for advanced applications; extraction; characterization; evaluation of the biological activity of bioactive principles from natural matrices
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

This Special Issue is devoted to the development of novel organic syntheses using transition metal complexes as catalysts. Transition metal catalysis is one of the most important and active areas in the field of modern organic synthesis, as it may allow the preparation of complex, multifunctionalized molecules in one step via the assembly of simple building blocks through an ordered sequence of mechanistic steps promoted by the metal center. The importance of this chemistry is continuously growing, and its huge synthetic impact will continue to attract the interest of scientists, both in academia and industry around the world.

Prof. Dr. Bartolo Gabriele
Guest Editor

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Keywords

  • catalysis
  • heterogeneous catalysis
  • homogeneous catalysis
  • metal-catalyzed reactions
  • organic synthesis promoted by metal catalysts

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Published Papers (8 papers)

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Editorial

Jump to: Research, Review

2 pages, 176 KiB  
Editorial
Organic Synthesis via Transition Metal-Catalysis
by Bartolo Gabriele
Molecules 2022, 27(4), 1227; https://doi.org/10.3390/molecules27041227 - 11 Feb 2022
Cited by 3 | Viewed by 2126
Abstract
In recent years, the development of transition-metal-catalyzed reactions has acquired an increasing importance [...] Full article
(This article belongs to the Special Issue Organic Synthesis via Transition Metal-Catalysis)

Research

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12 pages, 3029 KiB  
Article
Reductive Hydroformylation of Isosorbide Diallyl Ether
by Jérémy Ternel, Adrien Lopes, Mathieu Sauthier, Clothilde Buffe, Vincent Wiatz, Hervé Bricout, Sébastien Tilloy and Eric Monflier
Molecules 2021, 26(23), 7322; https://doi.org/10.3390/molecules26237322 - 2 Dec 2021
Cited by 13 | Viewed by 2233
Abstract
Isosorbide and its functionalized derivatives have numerous applications as bio-sourced building blocks. In this context, the synthesis of diols from isosorbide diallyl ether by hydrohydroxymethylation reaction is of extreme interest. This hydrohydroxymethylation, which consists of carbon-carbon double bonds converting into primary alcohol functions, [...] Read more.
Isosorbide and its functionalized derivatives have numerous applications as bio-sourced building blocks. In this context, the synthesis of diols from isosorbide diallyl ether by hydrohydroxymethylation reaction is of extreme interest. This hydrohydroxymethylation, which consists of carbon-carbon double bonds converting into primary alcohol functions, can be obtained by a hydroformylation reaction followed by a hydrogenation reaction. In this study, reductive hydroformylation was achieved using isosorbide diallyl ether as a substrate in a rhodium/amine catalytic system. The highest yield in bis-primary alcohols obtained was equal to 79%. Full article
(This article belongs to the Special Issue Organic Synthesis via Transition Metal-Catalysis)
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23 pages, 3386 KiB  
Article
Vanadium(IV) Complexes with Methyl-Substituted 8-Hydroxyquinolines: Catalytic Potential in the Oxidation of Hydrocarbons and Alcohols with Peroxides and Biological Activity
by Joanna Palion-Gazda, André Luz, Luis R. Raposo, Katarzyna Choroba, Jacek E. Nycz, Alina Bieńko, Agnieszka Lewińska, Karol Erfurt, Pedro V. Baptista, Barbara Machura, Alexandra R. Fernandes, Lidia S. Shul’pina, Nikolay S. Ikonnikov and Georgiy B. Shul’pin
Molecules 2021, 26(21), 6364; https://doi.org/10.3390/molecules26216364 - 21 Oct 2021
Cited by 6 | Viewed by 2980
Abstract
Methyl-substituted 8-hydroxyquinolines (Hquin) were successfully used to synthetize five-coordinated oxovanadium(IV) complexes: [VO(2,6-(Me)2-quin)2] (1), [VO(2,5-(Me)2-quin)2] (2) and [VO(2-Me-quin)2] (3). Complexes 1–3 demonstrated high catalytic activity in [...] Read more.
Methyl-substituted 8-hydroxyquinolines (Hquin) were successfully used to synthetize five-coordinated oxovanadium(IV) complexes: [VO(2,6-(Me)2-quin)2] (1), [VO(2,5-(Me)2-quin)2] (2) and [VO(2-Me-quin)2] (3). Complexes 1–3 demonstrated high catalytic activity in the oxidation of hydrocarbons with H2O2 in acetonitrile at 50 °C, in the presence of 2-pyrazinecarboxylic acid (PCA) as a cocatalyst. The maximum yield of cyclohexane oxidation products attained was 48%, which is high in the case of the oxidation of saturated hydrocarbons. The reaction leads to the formation of a mixture of cyclohexyl hydroperoxide, cyclohexanol and cyclohexanone. When triphenylphosphine is added, cyclohexyl hydroperoxide is completely converted to cyclohexanol. Consideration of the regio- and bond-selectivity in the oxidation of n-heptane and methylcyclohexane, respectively, indicates that the oxidation proceeds with the participation of free hydroxyl radicals. The complexes show moderate activity in the oxidation of alcohols. Complexes 1 and 2 reduce the viability of colorectal (HCT116) and ovarian (A2780) carcinoma cell lines and of normal dermal fibroblasts without showing a specific selectivity for cancer cell lines. Complex 3 on the other hand, shows a higher cytotoxicity in a colorectal carcinoma cell line (HCT116), a lower cytotoxicity towards normal dermal fibroblasts and no effect in an ovarian carcinoma cell line (order of magnitude HCT116 > fibroblasts > A2780). Full article
(This article belongs to the Special Issue Organic Synthesis via Transition Metal-Catalysis)
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14 pages, 7248 KiB  
Article
A Zinc-Mediated Deprotective Annulation Approach to New Polycyclic Heterocycles
by Lucia Veltri, Roberta Amuso, Marzia Petrilli, Corrado Cuocci, Maria A. Chiacchio, Paola Vitale and Bartolo Gabriele
Molecules 2021, 26(8), 2318; https://doi.org/10.3390/molecules26082318 - 16 Apr 2021
Cited by 4 | Viewed by 3196
Abstract
A straightforward approach to new polycyclic heterocycles, 1H-benzo[4,5]imidazo[1,2-c][1,3]oxazin-1-ones, is presented. It is based on the ZnCl2-promoted deprotective 6-endo-dig heterocyclization of N-Boc-2-alkynylbenzimidazoles under mild conditions (CH2Cl2, 40 °C for 3 [...] Read more.
A straightforward approach to new polycyclic heterocycles, 1H-benzo[4,5]imidazo[1,2-c][1,3]oxazin-1-ones, is presented. It is based on the ZnCl2-promoted deprotective 6-endo-dig heterocyclization of N-Boc-2-alkynylbenzimidazoles under mild conditions (CH2Cl2, 40 °C for 3 h). The zinc center plays a dual role, as it promotes Boc deprotection (with formation of the tert-butyl carbocation, which can be trapped by substrates bearing a nucleophilic group) and activates the triple bond toward intramolecular nucleophilic attack by the carbamate group. The structure of representative products has been confirmed by X-ray diffraction analysis. Full article
(This article belongs to the Special Issue Organic Synthesis via Transition Metal-Catalysis)
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17 pages, 2103 KiB  
Article
Sulfoximines-Assisted Rh(III)-Catalyzed C–H Activation and Intramolecular Annulation for the Synthesis of Fused Isochromeno-1,2-Benzothiazines Scaffolds under Room Temperature
by Bao Wang, Xu Han, Jian Li, Chunpu Li and Hong Liu
Molecules 2020, 25(11), 2515; https://doi.org/10.3390/molecules25112515 - 28 May 2020
Cited by 15 | Viewed by 3566
Abstract
A mild and facile Cp*Rh(III)-catalyzed C–H activation and intramolecular cascade annulation protocol has been proposed for the furnishing of highly fused isochromeno-1,2-benzothiazines scaffolds using S-phenylsulfoximides and 4-diazoisochroman-3-imine as substrates under room temperature. This method features diverse substituents and functional groups tolerance and [...] Read more.
A mild and facile Cp*Rh(III)-catalyzed C–H activation and intramolecular cascade annulation protocol has been proposed for the furnishing of highly fused isochromeno-1,2-benzothiazines scaffolds using S-phenylsulfoximides and 4-diazoisochroman-3-imine as substrates under room temperature. This method features diverse substituents and functional groups tolerance and relatively mild reaction conditions with moderate to excellent yields. Additionally, retentive configuration of sulfoximides in the conversion has been verified. Full article
(This article belongs to the Special Issue Organic Synthesis via Transition Metal-Catalysis)
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9 pages, 1909 KiB  
Communication
Synthesis of Functionalized Indoles via Palladium-Catalyzed Cyclization of N-(2-allylphenyl) Benzamide: A Method for Synthesis of Indomethacin Precursor
by Zhe Chang, Tong Ma, Yu Zhang, Zheng Dong, Heng Zhao and Depeng Zhao
Molecules 2020, 25(5), 1233; https://doi.org/10.3390/molecules25051233 - 9 Mar 2020
Cited by 8 | Viewed by 4492
Abstract
We developed an efficient method for synthesis of substituted N-benzoylindole via Pd(II)-catalyzed C–H functionalization of substituted N-(2-allylphenyl)benzamide. The reaction showed a broad substrate scope (including N-acetyl and N-Ts substrates) and substituted indoles were obtained in good to excellent yields. [...] Read more.
We developed an efficient method for synthesis of substituted N-benzoylindole via Pd(II)-catalyzed C–H functionalization of substituted N-(2-allylphenyl)benzamide. The reaction showed a broad substrate scope (including N-acetyl and N-Ts substrates) and substituted indoles were obtained in good to excellent yields. The most distinctive feature of this method lies in the high selectivity for N-benzoylindole over benzoxazine, and this is the first example of Pd(II)-catalyzed synthesis of substituted N-benzoylindole. Notably, this new method was applied for the synthesis of key intermediate of indomethacin. Full article
(This article belongs to the Special Issue Organic Synthesis via Transition Metal-Catalysis)
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Review

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19 pages, 5858 KiB  
Review
Direct Arylation in the Presence of Palladium Pincer Complexes
by Garazi Urgoitia, Maria Teresa Herrero, Fátima Churruca, Nerea Conde and Raul SanMartin
Molecules 2021, 26(14), 4385; https://doi.org/10.3390/molecules26144385 - 20 Jul 2021
Cited by 12 | Viewed by 4192
Abstract
Direct arylation is an atom-economical alternative to more established procedures such as Stille, Suzuki or Negishi arylation reactions. In comparison with other palladium sources and ligands, the use of palladium pincer complexes as catalysts or pre-catalysts for direct arylation has resulted in improved [...] Read more.
Direct arylation is an atom-economical alternative to more established procedures such as Stille, Suzuki or Negishi arylation reactions. In comparison with other palladium sources and ligands, the use of palladium pincer complexes as catalysts or pre-catalysts for direct arylation has resulted in improved efficiency, higher reaction yields, and advantageous reaction conditions. In addition to a revision of the literature concerning intra- and intermolecular direct arylation reactions performed in the presence of palladium pincer complexes, the role of these remarkably active catalysts will also be discussed. Full article
(This article belongs to the Special Issue Organic Synthesis via Transition Metal-Catalysis)
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35 pages, 9842 KiB  
Review
Rhodium-Catalyzed Synthesis of Organosulfur Compounds Involving S-S Bond Cleavage of Disulfides and Sulfur
by Mieko Arisawa and Masahiko Yamaguchi
Molecules 2020, 25(16), 3595; https://doi.org/10.3390/molecules25163595 - 7 Aug 2020
Cited by 21 | Viewed by 5902
Abstract
Organosulfur compounds are widely used for the manufacture of drugs and materials, and their synthesis in general conventionally employs nucleophilic substitution reactions of thiolate anions formed from thiols and bases. To synthesize advanced functional organosulfur compounds, development of novel synthetic methods is an [...] Read more.
Organosulfur compounds are widely used for the manufacture of drugs and materials, and their synthesis in general conventionally employs nucleophilic substitution reactions of thiolate anions formed from thiols and bases. To synthesize advanced functional organosulfur compounds, development of novel synthetic methods is an important task. We have been studying the synthesis of organosulfur compounds by transition-metal catalysis using disulfides and sulfur, which are easier to handle and less odiferous than thiols. In this article, we describe our development that rhodium complexes efficiently catalyze the cleavage of S-S bonds and transfer organothio groups to organic compounds, which provide diverse organosulfur compounds. The synthesis does not require use of bases or organometallic reagents; furthermore, it is reversible, involving chemical equilibria and interconversion reactions. Full article
(This article belongs to the Special Issue Organic Synthesis via Transition Metal-Catalysis)
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