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Molecules
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Halogen-Controlled Synthesis of Useful Organic Molecules
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Halogen-Controlled Synthesis of Useful Organic Molecules

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

Deadline for manuscript submissions: closed (30 September 2023) | Viewed by 24794

Special Issue Editors

Prof. Dr. Toshifumi Dohi

E-Mail Website
Guest Editor
Graduate School of Pharmaceutical Sciences, Ritsumeikan University, Shiga 525-8577, Japan
Interests: hypervalent iodine chemistry and its application; oxidation; coupling; heterocycle synthesis; asymmetric synthesis
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Cheng-Pan Zhang

E-Mail Website
Guest Editor
School of Chemistry, Chemical Engineering and Life Science, Wuhan University of Technology, 205 Luoshi Road, Wuhan 430070, China
Interests: the synthesis and reactivity of arylsulfonium salts; the development of novel transition-metal-catalyzed or -free fluorination and fluoroalkylation reactions

Special Issue Information

Dear Colleagues,

Halogens can be incorporated into many useful organic molecules and fine chemicals utilized in a wide range of scientific fields, such as natural products, biologically active compounds, and organic materials. In organic synthesis, halogen-including molecules have played distinct roles as synthetic intermediates for various transformations as well as the chemical reagents and catalysts for efficient halogen introductions and other synthetic transformations, such as oxidations and coupling reactions. Furthermore, unique transformations of organic substrates bearing halogen atoms have recently appeared in the literature, which includes new strategies and concepts for reaction designs controlled by the sizes and oxidation states of halogen groups. Interestingly, the number of halogens incorporated in organic molecules would sometimes alter the course of the reactions (for example, see the lactonization in Asian J. Org, Chem. 2015, 4, 1065.)

This Special Issue will highlight recent opportunities and new concepts in halogen-controlled organic synthesis (reagent and substrate controls) for their continuous development in future studies. We welcome review and original research articles associated with recent achievements in this area, for example, new strategies for organic transformation controlled by halogen groups and reagents, design of new halogen-based reagents and catalysts for selective synthesis, asymmetric transformation by chiral halogen reagents and catalysts, effective synthesis of useful halogen reagents and compound, and unique synthetic intermediate bearing halogen groups. Areas to be covered in this Special Issue may include, but are not limited to the extension of the known synthetic strategy and reaction for the new construction of organic molecules and for application to the useful organic compounds, i.e., bioactive molecules and organic materials.

Prof. Dr. Toshifumi Dohi
Prof. Dr. Cheng-Pan Zhang
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Halogens
  • Halogen-based reagents
  • Hypervalent compound
  • New synthetic transformation
  • Selective transformation
  • Unique halogenated substrates
  • Bioactive compounds
  • Organic materials

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Published Papers (5 papers)

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Research

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18 pages, 2119 KiB  
Article
Catalyst-Free Trans-Selective Oxyiodination and Oxychlorination of Alkynes Employing N–X (Halogen) Reagents
by Jiaqiong Sun, Yunliang Guo, Jiuli Xia, Guangfan Zheng and Qian Zhang
Molecules 2023, 28(21), 7420; https://doi.org/10.3390/molecules28217420 - 3 Nov 2023
Cited by 1 | Viewed by 997
Abstract
β-halogenated enol esters and ethers are versatile building blocks in organic synthesis, which has attracted increasing attention. In this study, we report the facile trans-oxyiodination and oxychlorination of alkynes, leading to the direct construction of versatile halogenated enol esters and ethers. This [...] Read more.
β-halogenated enol esters and ethers are versatile building blocks in organic synthesis, which has attracted increasing attention. In this study, we report the facile trans-oxyiodination and oxychlorination of alkynes, leading to the direct construction of versatile halogenated enol esters and ethers. This transformation features an easy operation, optimal atomic economy, a strong functional group tolerance, broad substrate scope, and excellent trans-selectivity. Employing highly electrophilic bifunctional N–X (halogen) reagents was the key to achieving broad reaction generality. To our knowledge, this transformation represents the first oxyhalogenation system employing N–X (halogen) reagents as both oxylation and halogenation sources. Full article
(This article belongs to the Special Issue Halogen-Controlled Synthesis of Useful Organic Molecules)
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Graphical abstract

16 pages, 1075 KiB  
Article
Markovnikov-Type Hydrotrifluoromethylchalcogenation of Unactivated Terminal Alkenes with [Me4N][XCF3] (X = S, Se) and TfOH
by Jin Shi and Cheng-Pan Zhang
Molecules 2020, 25(19), 4535; https://doi.org/10.3390/molecules25194535 - 3 Oct 2020
Cited by 11 | Viewed by 3188
Abstract
The first Markovnikov-type hydrotrifluoromethylselenolation of unactivated terminal alkenes with the readily accessible [Me4N][SeCF3] reagent and the superacid TfOH is reported. The reaction proceeded at room temperature under catalyst- and additive-free conditions to give the branched trifluoromethylselenolated products in good [...] Read more.
The first Markovnikov-type hydrotrifluoromethylselenolation of unactivated terminal alkenes with the readily accessible [Me4N][SeCF3] reagent and the superacid TfOH is reported. The reaction proceeded at room temperature under catalyst- and additive-free conditions to give the branched trifluoromethylselenolated products in good yields. This protocol is also applicable to the Markovnikov-type hydrotrifluoromethylthiolation of unactivated terminal alkenes using [Me4N][SCF3]/TfOH, but not to the hydrotrifluoromethoxylation with CsOCF3/TfOH under the same conditions. The successful hydrotrifluoromethylselenolation and hydrotrifluoromethylthiolation showed simplicity and high regioselectivity, taming the sensitive −XCF3 (X = Se, S) anions with TfOH, and offered a convenient method for the straightforward synthesis of branched trifluoromethyl selenoethers and thioethers from unactivated alkenes. Full article
(This article belongs to the Special Issue Halogen-Controlled Synthesis of Useful Organic Molecules)
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Scheme 1

Review

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44 pages, 26229 KiB  
Review
Aryl-, Akynyl-, and Alkenylbenziodoxoles: Synthesis and Synthetic Applications
by Irina A. Mironova, Dmitrii M. Noskov, Akira Yoshimura, Mekhman S. Yusubov and Viktor V. Zhdankin
Molecules 2023, 28(5), 2136; https://doi.org/10.3390/molecules28052136 - 24 Feb 2023
Cited by 18 | Viewed by 2588
Abstract
Hypervalent iodine reagents are in high current demand due to their exceptional reactivity in oxidative transformations, as well as in diverse umpolung functionalization reactions. Cyclic hypervalent iodine compounds, known under the general name of benziodoxoles, possess improved thermal stability and synthetic versatility in [...] Read more.
Hypervalent iodine reagents are in high current demand due to their exceptional reactivity in oxidative transformations, as well as in diverse umpolung functionalization reactions. Cyclic hypervalent iodine compounds, known under the general name of benziodoxoles, possess improved thermal stability and synthetic versatility in comparison with their acyclic analogs. Aryl-, alkenyl-, and alkynylbenziodoxoles have recently received wide synthetic applications as efficient reagents for direct arylation, alkenylation, and alkynylation under mild reaction conditions, including transition metal-free conditions as well as photoredox and transition metal catalysis. Using these reagents, a plethora of valuable, hard-to-reach, and structurally diverse complex products can be synthesized by convenient procedures. The review covers the main aspects of the chemistry of benziodoxole-based aryl-, alkynyl-, and alkenyl- transfer reagents, including preparation and synthetic applications. Full article
(This article belongs to the Special Issue Halogen-Controlled Synthesis of Useful Organic Molecules)
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Graphical abstract

33 pages, 15917 KiB  
Review
Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy
by Hideyasu China, Ravi Kumar, Kotaro Kikushima and Toshifumi Dohi
Molecules 2020, 25(24), 6007; https://doi.org/10.3390/molecules25246007 - 18 Dec 2020
Cited by 27 | Viewed by 4765
Abstract
In organic synthesis, due to their high electrophilicity and leaving group properties, halogens play pivotal roles in the activation and structural derivations of organic compounds. Recently, cyclizations induced by halogen groups that allow the production of diverse targets and the structural reorganization of [...] Read more.
In organic synthesis, due to their high electrophilicity and leaving group properties, halogens play pivotal roles in the activation and structural derivations of organic compounds. Recently, cyclizations induced by halogen groups that allow the production of diverse targets and the structural reorganization of organic molecules have attracted significant attention from synthetic chemists. Electrophilic halogen atoms activate unsaturated and saturated hydrocarbon moieties by generating halonium intermediates, followed by the attack of carbon-containing, nitrogen-containing, oxygen-containing, and sulfur-containing nucleophiles to give highly functionalized carbocycles and heterocycles. New transformations of halogenated organic molecules that can control the formation and stereoselectivity of the products, according to the difference in the size and number of halogen atoms, have recently been discovered. These unique cyclizations may possibly be used as efficient synthetic strategies with future advances. In this review, innovative reactions controlled by halogen groups are discussed as a new concept in the field of organic synthesis. Full article
(This article belongs to the Special Issue Halogen-Controlled Synthesis of Useful Organic Molecules)
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Figure 1

24 pages, 7061 KiB  
Review
Tetrabutylammonium Bromide (TBAB) Catalyzed Synthesis of Bioactive Heterocycles
by Bimal Krishna Banik, Bubun Banerjee, Gurpreet Kaur, Shivam Saroch and Rajat Kumar
Molecules 2020, 25(24), 5918; https://doi.org/10.3390/molecules25245918 - 14 Dec 2020
Cited by 48 | Viewed by 11980
Abstract
During the last two decades, tetrabutylammonium bromide (TBAB) has gained significant attention as an efficient metal-free homogeneous phase-transfer catalyst. A catalytic amount of TBAB is sufficient to catalyze various alkylation, oxidation, reduction, and esterification processes. It is also employed as an efficient co-catalyst [...] Read more.
During the last two decades, tetrabutylammonium bromide (TBAB) has gained significant attention as an efficient metal-free homogeneous phase-transfer catalyst. A catalytic amount of TBAB is sufficient to catalyze various alkylation, oxidation, reduction, and esterification processes. It is also employed as an efficient co-catalyst for numerous coupling reactions. It has also acted as an efficient zwitterionic solvent in many organic transformations under molten conditions. In this review, we have summarized the recent developments on TBAB-catalyzed protocols for the efficient synthesis of various biologically promising heterocyclic scaffolds. Full article
(This article belongs to the Special Issue Halogen-Controlled Synthesis of Useful Organic Molecules)
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