Palladium-Catalyzed γ-C(sp3 )-H Arylation of Thiols by a Detachable Protecting/Directing Group
Likun Jin1,2, Jianchun Wang1, Guangbin Dong1
1Department of Chemistry, University of Chicago, Chicago, IL, 60637, USA.
Abstract:
Reported herein is a palladium-catalyzed, directed γ-C(sp3 )-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.
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