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

ABSTRACT: 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.

SUBMITTER: Tan E

PROVIDER: S-EPMC5838643 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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

Tan Eric E Quinonero Ophélie O Elena de Orbe M M Echavarren Antonio M AM

ACS catalysis 20180129 3

We report the alkynylation of C(sp<sup>2</sup>)-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. ...[more]

PMID: 29527402

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