Radical-Mediated Functionalization of Alkenes

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalysis in Organic and Polymer Chemistry".

Deadline for manuscript submissions: closed (30 April 2023) | Viewed by 4955

Special Issue Editors


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Guest Editor
Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China
Interests: difunctionalization of alkenes; radical chemistry; electrochemistry

E-Mail Website
Guest Editor
Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China
Interests: radical chemistry; photochemistry; difunctionalization of alkenes; C-H functionalization

Special Issue Information

Dear Colleagues,

Functionalization of alkenes is an attractive strategy to rapidly install two functional group or build two bonds, thus offering an ideal step-economic construction for the generation of complex molecules. However, the vast majority of alkene functionalization approaches focus on the merger of the classical cross-couplings, which suffer from requiring expensive nucleophilic and electrophilic functional reagents, such as organometallic species and organohalides, for inserting the C-C double bonds in the presence of noble transition metals and/or ligands. Thus, functionalization of alkenes initiated by radical process is a particularly attractive approach, which allows to avoid the use of transition metals and complex precursors via C–H functionalization.

In this special issue, we welcome reports on radical-mediated functionalization of olefins from various fields, including metal-free conditions, metal catalysis, organocatalysis, photocatalysis, or electrocatalysis, among others. These reactions can also be carried out involving any radical precursor, including alkyl radicals, aryl radicals, nitrogen radicals, oxygen radicals, selenium radicals, sulfur radicals and alkene-derived radical cations, among others.

Prof. Dr. Renjie Song
Dr. Xuanhui Ouyang
Guest Editors

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Keywords

  • radical reaction
  • functionalization of alkenes
  • C-H functionalization
  • photochemistry
  • electrochemistry

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Published Papers (3 papers)

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Research

14 pages, 5297 KiB  
Article
Metal-Free Photoredox Intramolecular Cyclization of N-Aryl Acrylamides
by Zhaosheng Liu, Xiaochen Ji, Feng Zhao, Guojun Deng and Huawen Huang
Catalysts 2023, 13(6), 1007; https://doi.org/10.3390/catal13061007 - 14 Jun 2023
Cited by 1 | Viewed by 1750
Abstract
A novel metal-free photoredox-catalyzed cyclization reaction of N-aryl acrylamide is herein reported that provides synthetically valuable oxindole derivatives through the bis-mediation of H2O and aldehyde. In this work, sustainable visible light was used as the energy source, and the organic [...] Read more.
A novel metal-free photoredox-catalyzed cyclization reaction of N-aryl acrylamide is herein reported that provides synthetically valuable oxindole derivatives through the bis-mediation of H2O and aldehyde. In this work, sustainable visible light was used as the energy source, and the organic light-emitting molecule 4CzIPN served as the efficient photocatalyst. The main characteristics of this reaction are environmentally friendly and high yields. Full article
(This article belongs to the Special Issue Radical-Mediated Functionalization of Alkenes)
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11 pages, 1310 KiB  
Article
Ferrous Salt-Catalyzed Oxidative Alkenylation of Indoles: Facile Access to 3-Alkylideneindolin-2-Ones
by Yunfei Tian, Luping Zheng, Ying Chen, Yufei Li, Mengna Wang, Weijun Fu and Zejiang Li
Catalysts 2023, 13(6), 930; https://doi.org/10.3390/catal13060930 - 25 May 2023
Viewed by 1249
Abstract
The direct oxidative alkenylation of indoles is achieved by ferrous salts under mild conditions, which provides one effective strategy for the synthesis of 3-alkylideneindolin-2-one in a single step. This reaction system features simple and readily available materials, mild conditions, and easy accessibility. The [...] Read more.
The direct oxidative alkenylation of indoles is achieved by ferrous salts under mild conditions, which provides one effective strategy for the synthesis of 3-alkylideneindolin-2-one in a single step. This reaction system features simple and readily available materials, mild conditions, and easy accessibility. The control experiments also demonstrate a radical pathway was involved in the reaction. Moreover, the method performs well on the gram-scale experiment, which indicates that this method enjoys a broad prospect in synthetic chemistry. Full article
(This article belongs to the Special Issue Radical-Mediated Functionalization of Alkenes)
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15 pages, 1640 KiB  
Article
Visible-Light-Induced Difunctionalization of the C-C Bond of Alkylidenecyclopropanes with Acyl Chlorides
by Chuan Ding, Peng-Fei Huang, Biquan Xiong, Ke-Wen Tang and Yu Liu
Catalysts 2023, 13(6), 919; https://doi.org/10.3390/catal13060919 - 23 May 2023
Cited by 1 | Viewed by 1656
Abstract
A new and powerful visible-light-induced difunctionalization of the C-C σ-bond of alkylidenecyclopropanes via a ring-opening process was developed. Importantly, acyl chlorides are used as both acyl and Cl sources. This strategy provides an effective route for the difunctionalization of the C-C bond with [...] Read more.
A new and powerful visible-light-induced difunctionalization of the C-C σ-bond of alkylidenecyclopropanes via a ring-opening process was developed. Importantly, acyl chlorides are used as both acyl and Cl sources. This strategy provides an effective route for the difunctionalization of the C-C bond with an acyl radical and Cl to construct a new C-C bond and a C-Cl bond in one pot. In addition, it has a wide range of substrates and can tolerate various functional groups. Full article
(This article belongs to the Special Issue Radical-Mediated Functionalization of Alkenes)
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