Selective Formation of Secondary Amides via the Copper-Catalyzed Cross-Coupling of Alkylboronic Acids with Primary Amides

Steven A. Rossi, Kirk W. Shimkin, Qun Xu, Luis M. Mori-Quiroz and Donald A. Watson*

*Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, United States, Email: dawatsonudel.edu

S. A. Rossi, K. W. Shimkin, Q. Xu, L. M. Mori-Quiroz, D. A. Watson, Org. Lett., 2013, 15, 2314-2317.

DOI: 10.1021/ol401004r

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Abstract

The key to the success of a general catalytic procedure for the cross-coupling of primary amides and alkylboronic acids 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.

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Key Words

Chan-Lam Coupling, Amides, DTBP

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ID: J54-Y2013