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Selective formation of secondary amides via the copper-catalyzed cross-coupling of alkylboronic acids with primary amides.

ABSTRACT: For the first time, a general catalytic procedure for the cross-coupling of primary amides and alkylboronic acids is demonstrated. The key to the success of this reaction was the identification of a mild base (NaOSiMe3) and oxidant (di-tert-butyl peroxide) to promote the copper-catalyzed reaction in high yield. This transformation provides a facile, high-yielding method for the monoalkylation of amides.

SUBMITTER: Rossi SA

PROVIDER: S-EPMC4265364 | biostudies-literature | 2013 May

REPOSITORIES: biostudies-literature

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Selective formation of secondary amides via the copper-catalyzed cross-coupling of alkylboronic acids with primary amides.

Rossi Steven A SA Shimkin Kirk W KW Xu Qun Q Mori-Quiroz Luis M LM Watson Donald A DA

Organic letters 20130423 9

For the first time, a general catalytic procedure for the cross-coupling of primary amides and alkylboronic acids is demonstrated. The key to the success of this reaction was the identification of a mild base (NaOSiMe3) and oxidant (di-tert-butyl peroxide) to promote the copper-catalyzed reaction in high yield. This transformation provides a facile, high-yielding method for the monoalkylation of amides. ...[more]

PMID: 23611591

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