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

• Published in: Angewandte Chemie International Edition Vol. 57; no. 22; pp. 6667 - 6671
• Main Authors: Xue, Fei, Wang, Falu, Liu, Jiazhen, Di, Jiamei, Liao, Qi, Lu, Huifang, Zhu, Min, He, Liping, He, Huan, Zhang, Dan, Song, Hao, Liu, Xiao‐Yu, Qin, Yong
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 28-05-2018
• Edition: International ed. in English
• Subjects: alkyl radicals; Catalysis; conjugate addition; desulfuration; Intermediates; Photoredox catalysis; radical reactions; Radicals; Substrates; radical reactions; alkyl radicals; photoredox catalysis; desulfuration; conjugate addition
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201802710

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.
Easy as 1°2°3°: A new desulfurative method for generating primary, secondary, and tertiary alkyl radicals through visible‐light photoredox catalysis is reported. The key process for forming the alkyl radical species involves the generation of N‐centered radicals from sulfinamide intermediates, followed by fragmentation.