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Photocatalyzed Metal-Free Alkylheteroarylation of Unactivated Olefins via Direct Acidic C(sp³)–H Bond Activation

Author:
Fang, Jie, Dong, Wan-Li, Xu, Guo-Qiang, Xu, Peng-Fei
Source:
Organic letters 2019 v.21 no.12 pp. 4480-4485
ISSN:
1523-7052
Subject:
acetonitrile, alkenes, carbon-hydrogen bond activation, chemical structure, chloroform, esters, ethylene dichloride, hydrogen, ketones, methylene chloride, photocatalysis
Abstract:
A visible-light-promoted metal-free alkylheteroarylation of unactivated olefins was developed by using readily available ketones/esters as the alkyl radical source. With this strategy, both linear and cyclic ketones/esters could be conveniently converted to corresponding α-carbonyl alkyl radical species by using commonly found diacylperoxide (LPO) as the hydrogen atom transfer reagent, and heteroaryl-containing 1,7-carbonyl compounds were synthesized via distal heteroaryl ipso-migration in good to excellent yields with high functional group tolerance and a broad substrate scope. In addition, this approach was also amenable to C–H functionalization of acetonitrile, dichloromethane, 1,2-dichloroethane, and chloroform.
Agid:
6478155