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Copper-Catalyzed β-Boration of α,β-Unsaturated Carbonyl Compounds with Tetrahydroxydiborane

Gary A. Molander* and Silas A. McKee

*Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States, Email: gmolandrsas.upenn.edu

G. A. Molander, S. A. McKee, Org. Lett., 2011, 13, 4648-4687.

DOI: 10.1021/ol201900d


Abstract

A copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane allows direct, efficient access to boronic acids and their derivatives. Various α,β-unsaturated amides, ketones and esters are converted to the corresponding β-trifluoroborato compounds in good to excellent yields.

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Suzuki-Miyaura Cross-Coupling of Potassium Trifluoroboratohomoenolates

G. A. Molander, D. E. Petrillo, Org. Lett., 2008, 10, 1795-1798.


Key Words

Trifluoroborates


ID: J54-Y2011-2520