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Palladium‐Catalyzed Picolinamide‐Directed Benzylic C( sp 3 )−H Chalcogenation with Diaryl Disulfides and Diphenyl Diselenide
Author(s) -
Wang Kai,
Hou Jiahao,
Zhang Changjun,
Cheng Ke,
Bai Renren,
Xie Yuanyuan
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000280
Subject(s) - chemistry , diselenide , palladium , diphenyl diselenide , thioether , catalysis , coupling reaction , substrate (aquarium) , medicinal chemistry , functional group , stereochemistry , photochemistry , organic chemistry , selenium , oceanography , geology , polymer
The first palladium‐catalyzed direct benzylic C( sp 3 )−H chalcogenation with diaryl disulfides and diphenyl diselenide has been established. The coupling reaction proceeds between the thioether radical and palladiumcycle intermediate. Picolinamide serves as an excellent directing group for the C−H activation of benzylic C( sp 3 )−H and can be easily removed. The current protocol exhibits a relatively broad substrate scope and high functional group compatibility. A mechanistic study indicates that palladium(IV) intermediate is probably formed during the course of the reaction.