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Palladium‐Catalyzed γ‐C(sp 3 )−H Arylation of Thiols by a Detachable Protecting/Directing Group
Author(s) -
Jin Likun,
Wang Jianchun,
Dong Guangbin
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201807760
Subject(s) - palladium , chemistry , sulfur , thiol , reagent , catalysis , functional group , protecting group , combinatorial chemistry , surface modification , organic chemistry , alkyl , polymer
Reported herein is a palladium‐catalyzed, directed γ‐C(sp 3 )−H arylation of protected thiols. The key is to utilize Michael acceptors as a dual reagent to install a protecting/directing group on thiols by a thiol‐Michael click reaction, and remove it later under basic conditions. The C−H arylation proceeds with high functional‐group tolerance and the deprotected thiols can be further transformed into other sulfur‐containing compounds. This unique mode of activation could open the door for site‐selective functionalization of thiols or other sulfur‐containing compounds at unactivated positions.