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Palladium-Catalyzed Preparation of Weinreb Amides from Boronic Acids and N-Methyl-N-methoxycarbamoyl Chloride

Ravi Krishnamoorthy, Sang Q. Lam, Christopher M. Manley and R. Jason Herr*

*Medicinal Chemistry Department, Albany Molecular Research, Inc. (AMRI), 26 Corporate Circle, P.O. Box 15098, Albany, New York 12212-5098, Email: rjason.herramriglobal.com

R. Krishnamoorthy, S. Q. Lam, C. M. Manley, R. J. Herr, J. Org. Chem., 2010, 75, 1251-1258.

DOI: 10.1021/jo902647h (free Supporting Information)


Abstract

A palladium-catalyzed cross-coupling reaction between organoboronic acids and commercially available N-methoxy-N-methylcarbamoyl chloride allows the synthesis of Weinreb benzamides and heteroaromatic analogues, as well as α,β-unsaturated Weinreb amides. This simple protocol is also applicable to the use of potassium organotrifluoroborates.

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Key Words

benzamides, α,β-unsaturated compounds, Weinreb amides


ID: J42-Y2010-0500