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Visible‐Light‐Induced Pyridylation of Remote C(sp 3 )−H Bonds by Radical Translocation of N‐Alkoxypyridinium Salts
Author(s) -
Kim Inwon,
Park Bohyun,
Kang Gyumin,
Kim Jiyun,
Jung Hoimin,
Lee Hyeonyeong,
Baik MuHyun,
Hong Sungwoo
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201809879
Subject(s) - alkoxy group , chemistry , photochemistry , nucleophile , substrate (aquarium) , alkyl , catalysis , visible spectrum , molecule , chromosomal translocation , radical ion , photoredox catalysis , stereochemistry , photocatalysis , medicinal chemistry , ion , materials science , organic chemistry , optoelectronics , oceanography , geology , biochemistry , gene
Metal‐free, visible‐light‐induced site‐selective heteroarylation of remote C(sp 3 )−H bonds has been accomplished through the design of N‐alkoxyheteroarenium salts serving as both alkoxy radical precursors and heteroaryl sources. The transient alkoxy radical can be generated by the single‐electron reduction of an N‐alkoxypyridinium substrate by a photoexcited quinolinone catalyst. Subsequent radical translocation of the alkoxy radical forms a nucleophilic alkyl radical intermediate, which undergoes addition to the substrate to achieve remote C(sp 3 )−H heteroarylation. This cascade strategy provides a powerful platform for remote C(sp 3 )−H heteroarylation in a controllable and selective manner and is well suited for late‐stage functionalization of complex bioactive molecules.