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

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journal contribution
posted on 29.01.2018 by Eric Tan, Ophélie Quinonero, M. Elena de Orbe, Antonio M. Echavarren
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.

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