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Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters.

ABSTRACT: A method for the direct methylation of aryl, heteroaryl, and vinyl boronate esters is reported, involving the reaction of iodomethane with aryl-, heteroaryl-, and vinylboronate esters catalyzed by palladium and PtBu2Me. This transformation occurs with a remarkably broad scope and is suitable for late-stage derivatization of biologically active compounds via the boronate esters. The unique capabilities of this method are demonstrated by combining carbon-boron bond-forming reactions with palladium-catalyzed methylation in a tandem transformation.

SUBMITTER: Haydl AM

PROVIDER: S-EPMC6827334 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters.

Haydl Alexander M AM Hartwig John F JF

Organic letters 20190214 5

A method for the direct methylation of aryl, heteroaryl, and vinyl boronate esters is reported, involving the reaction of iodomethane with aryl-, heteroaryl-, and vinylboronate esters catalyzed by palladium and PtBu<sub>2</sub>Me. This transformation occurs with a remarkably broad scope and is suitable for late-stage derivatization of biologically active compounds via the boronate esters. The unique capabilities of this method are demonstrated by combining carbon-boron bond-forming reactions wit ...[more]

PMID: 30763109

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