Literature DB >> 29671934

A Desulfurative Strategy for the Generation of Alkyl Radicals Enabled by Visible-Light Photoredox Catalysis.

Fei Xue1, Falu Wang1, Jiazhen Liu1, Jiamei Di1, Qi Liao1, Huifang Lu1, Min Zhu1, Liping He1, Huan He1, Dan Zhang1, Hao Song1, Xiao-Yu Liu1, Yong Qin1.   

Abstract

Herein, we present a new desulfurative method for generating primary, secondary, and tertiary alkyl radicals through visible-light photoredox catalysis. A process that involves the generation of N-centered radicals from sulfinamide intermediates, followed by subsequent fragmentation, is critical to forming the corresponding alkyl radical species. This strategy has been successfully applied to conjugate addition reactions that features mild reaction conditions, broad substrate scope (>60 examples), and good functional-group tolerance.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkyl radicals; conjugate addition; desulfuration; photoredox catalysis; radical reactions

Year:  2018        PMID: 29671934     DOI: 10.1002/anie.201802710

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  5 in total

Review 1.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

Review 2.  Photocatalytic C(sp3) radical generation via C-H, C-C, and C-X bond cleavage.

Authors:  Chia-Yu Huang; Jianbin Li; Chao-Jun Li
Journal:  Chem Sci       Date:  2022-04-18       Impact factor: 9.969

Review 3.  Strategies for the direct oxidative esterification of thiols with alcohols.

Authors:  Manzarbanou Asnaashariisfahani; Bayan Azizi; Mohammad Reza Poor Heravi; Elham Mohammadi; Sattar Arshadi; Esmail Vessally
Journal:  RSC Adv       Date:  2022-05-13       Impact factor: 4.036

4.  Sulfinamide Synthesis Using Organometallic Reagents, DABSO, and Amines.

Authors:  Pui Kin Tony Lo; Gwyndaf A Oliver; Michael C Willis
Journal:  J Org Chem       Date:  2020-04-14       Impact factor: 4.354

5.  Generation of Alkyl Radicals: From the Tyranny of Tin to the Photon Democracy.

Authors:  Stefano Crespi; Maurizio Fagnoni
Journal:  Chem Rev       Date:  2020-08-06       Impact factor: 60.622

  5 in total

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