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Catalytic Radical Reactions
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Catalytic Radical Reactions

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

Deadline for manuscript submissions: closed (30 June 2023) | Viewed by 11413

Special Issue Editor

Dr. Huan-Ming Huang

E-Mail Website
Guest Editor
School of Physical Science and Technology, ShanghaiTech University, Shanghai, China
Interests: radical chemistry; sustainable catalysis; drug design & synthesis; synthetic methodology

Special Issue Information

Dear Colleagues,

Catalytic radical reactions including photoredox chemistry, electrosynthesis, photoelectrochemistry, metallaphotoredox catalysis, dual catalysis, and transition metal catalysis have already become an emerging topic in synthetic chemistry and utilized in medicinal chemistry.

In this Special Issue on “Catalytic Radical Reactions”, we invite papers related to synthetic methodology, complex architecture synthesis, mechanistic study, material synthesis, total synthesis, and computational studies involving different types of catalytic radical reactions. We will highlight emerging areas in radical chemistry and inspire future development toward modern synthetic chemistry.

Dr. Huan-Ming Huang
Guest Editor

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

  • radical
  • photoredox chemistry
  • electrosynthesis
  • transition metal catalysis
  • enantioselective
  • cross-couplings
  • visible light
  • cascade reaction

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Published Papers (4 papers)

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Research

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12 pages, 4837 KiB  
Article
Diphenyl Diselenide-Assisted Radical Addition Reaction of Diphenyl Disulfide to Unsaturated Bonds upon Photoirradiation
by Yuki Yamamoto, Qiqi Chen and Akiya Ogawa
Molecules 2023, 28(6), 2450; https://doi.org/10.3390/molecules28062450 - 7 Mar 2023
Cited by 2 | Viewed by 2547
Abstract
The addition reaction of interelement compounds with heteroatom–heteroatom single bonds to unsaturated bonds under photoirradiation is an important method for the efficient and atom-economical construction of carbon–heteroatom bonds. However, in practice, the desired addition reaction is sometimes unable to proceed as expected due [...] Read more.
The addition reaction of interelement compounds with heteroatom–heteroatom single bonds to unsaturated bonds under photoirradiation is an important method for the efficient and atom-economical construction of carbon–heteroatom bonds. However, in practice, the desired addition reaction is sometimes unable to proceed as expected due to the low efficiency of the desired addition reactions or the preferential polymerization of unsaturated compounds. In this study, by combining an interelement compound with homologous heteroatom compounds as a catalyst, we succeeded in suppressing the polymerization of the unsaturated compounds and in attaining a highly selective carbon–heteroatom bond formation through the desired addition reaction. In this paper, we have examined in detail whether such a “catalytic radical reaction” proceeds for unsaturated compounds and found that the dithiolation of some unsaturated compounds (i.e., vinylic ethers, styrenes, and isocyanides) could proceed with the assistance of (PhSe)2 under light. The developed methods in this study are expected to have strong implications in the fields of radical chemistry, heteroatom chemistry, synthetic organic chemistry, and catalyst chemistry as atom-economical methods for carbon–heteroatom bond formation. Full article
(This article belongs to the Special Issue Catalytic Radical Reactions)
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Review

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128 pages, 31070 KiB  
Review
Recent Advances in the Enantioselective Radical Reactions
by Tomasz Bauer, Yusuf Zaim Hakim and Paulina Morawska
Molecules 2023, 28(17), 6252; https://doi.org/10.3390/molecules28176252 - 25 Aug 2023
Cited by 7 | Viewed by 2582
Abstract
The review covers research published since 2017 and is focused on enantioselective synthesis using radical reactions. It describes recent approaches to the asymmetric synthesis of chiral molecules based on the application of the metal catalysis, dual metal and organocatalysis and finally, pure organocatalysis [...] Read more.
The review covers research published since 2017 and is focused on enantioselective synthesis using radical reactions. It describes recent approaches to the asymmetric synthesis of chiral molecules based on the application of the metal catalysis, dual metal and organocatalysis and finally, pure organocatalysis including enzyme catalysis. This review focuses on the synthetic aspects of the methodology and tries to show which compounds can be obtained in enantiomerically enriched forms. Full article
(This article belongs to the Special Issue Catalytic Radical Reactions)
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46 pages, 12655 KiB  
Review
Remote Radical 1,3-, 1,4-, 1,5-, 1,6- and 1,7-Difunctionalization Reactions
by Xiaoming Ma, Qiang Zhang and Wei Zhang
Molecules 2023, 28(7), 3027; https://doi.org/10.3390/molecules28073027 - 28 Mar 2023
Cited by 18 | Viewed by 3053
Abstract
Radical transformations are powerful in organic synthesis for the construction of molecular scaffolds and introduction of functional groups. In radical difunctionalization reactions, the radicals in the first functionalized intermediates can be relocated through resonance, hydrogen atom or group transfer, and ring opening. The [...] Read more.
Radical transformations are powerful in organic synthesis for the construction of molecular scaffolds and introduction of functional groups. In radical difunctionalization reactions, the radicals in the first functionalized intermediates can be relocated through resonance, hydrogen atom or group transfer, and ring opening. The resulting radical intermediates can undertake the following paths for the second functionalization: (1) couple with other radical groups, (2) oxidize to cations and then react with nucleophiles, (3) reduce to anions and then react with electrophiles, (4) couple with metal-complexes. The rearrangements of radicals provide the opportunity for the synthesis of 1,3-, 1,4-, 1,5-, 1,6-, and 1,7-difunctionalization products. Multiple ways to initiate the radical reaction coupling with intermediate radical rearrangements make the radical reactions good for difunctionalization at the remote positions. These reactions offer the advantages of synthetic efficiency, operation simplicity, and product diversity. Full article
(This article belongs to the Special Issue Catalytic Radical Reactions)
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Graphical abstract

46 pages, 13274 KiB  
Review
Recent Advances in Catalytic and Technology-Driven Radical Addition to N,N-Disubstituted Iminium Species
by Sylvain Oudeyer, Vincent Levacher, Hélène Beucher and Jean-François Brière
Molecules 2023, 28(3), 1071; https://doi.org/10.3390/molecules28031071 - 20 Jan 2023
Cited by 4 | Viewed by 2615
Abstract
Recently, radical chemistry has grown exponentially in the toolbox of organic synthetic chemists. Upon the (re)introduction of modern catalytic and technology-driven strategies, the implementation of highly reactive radical species is currently facilitated while expanding the scope of numerous synthetic methodologies. In this context, [...] Read more.
Recently, radical chemistry has grown exponentially in the toolbox of organic synthetic chemists. Upon the (re)introduction of modern catalytic and technology-driven strategies, the implementation of highly reactive radical species is currently facilitated while expanding the scope of numerous synthetic methodologies. In this context, this review intends to cover the recent advances in radical-based transformations of N,N-disubstituted iminium substrates that encompass unique reactivities with respect to imines or protonated iminium salts. In particular, we have focused on the literature concerning the dipole type substrates, such as nitrones or azomethine imines, together with the chemistry of N+-X− (X = O, NR) azaarenium dipoles, which proved to be very versatile platforms in that field of research. The N-alkylazaarenium salts were been considered, which demonstrated specific reactivity profiles in radical chemistry. Full article
(This article belongs to the Special Issue Catalytic Radical Reactions)
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