Broad-Scope Rh-Catalyzed Inverse-Sonogashira Reaction Directed by Weakly Coordinating Groups

We report the alkynylation of C­(sp2)–H bonds with bromoalkynes (inverse-Sonogashira reaction) directed by synthetically useful ester, ketone, and ether groups under rhodium catalysis. Other less common directing groups such as amine, thioether, sulfoxide, sulfone, phenol ester, and carbamate are al...

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Bibliographic Details
Published in:ACS catalysis 2018-03, Vol.8 (3), p.2166-2172
Main Authors: Tan, Eric, Quinonero, Ophélie, Elena de Orbe, M, Echavarren, Antonio M
Format: Article
Language:English
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Summary:We report the alkynylation of C­(sp2)–H bonds with bromoalkynes (inverse-Sonogashira reaction) directed by synthetically useful ester, ketone, and ether groups under rhodium catalysis. Other less common directing groups such as amine, thioether, sulfoxide, sulfone, phenol ester, and carbamate are also suitable directing groups. Mechanistic studies indicate that the reaction proceeds by a turnover-limiting C–H activation step via an electrophilic-type substitution.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.7b04395