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Ligand-accelerated ortho-C-H alkylation of arylcarboxylic acids using alkyl boron reagents.

ABSTRACT: A protocol for the Pd(II)-catalyzed ortho-C-H alkylation of phenylacetic and benzoic acids using alkylboron reagents is disclosed. Monoprotected amino acid ligands (MPAA) were found to significantly promote reactivity. Both potassium alkyltrifluoroborates and alkylboronic acids were compatible coupling partners. The possibility of a radical alkyl transfer to Pd(II) was also investigated.

SUBMITTER: Thuy-Boun PS

PROVIDER: S-EPMC3879047 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature

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Ligand-accelerated ortho-C-H alkylation of arylcarboxylic acids using alkyl boron reagents.

Thuy-Boun Peter S PS Villa Giorgio G Dang Devin D Richardson Paul P Su Shun S Yu Jin-Quan JQ

Journal of the American Chemical Society 20131108 46

A protocol for the Pd(II)-catalyzed ortho-C-H alkylation of phenylacetic and benzoic acids using alkylboron reagents is disclosed. Monoprotected amino acid ligands (MPAA) were found to significantly promote reactivity. Both potassium alkyltrifluoroborates and alkylboronic acids were compatible coupling partners. The possibility of a radical alkyl transfer to Pd(II) was also investigated. ...[more]

PMID: 24124892

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