Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 38, Pages 12352-12355Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201807760
Keywords
arylation; C-H activation; directing groups; palladium; thiols
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Funding
- Frasch Foundation
- University of Chicago
- China Scholarship Council [201606840070]
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Reported herein is a palladium-catalyzed, directed gamma-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.
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