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 (free Supporting Information)
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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