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Highly Stereoselective Synthesis of cis-Alkenyl Pinacolboronates and Potassium cis-Alkenyltrifluoroborates via a Hydroboration/Protodeboronation Approach

Gary A. Molander* and Noel M. Ellis

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

G. A. Molander, N. M. Ellis, J. Org. Chem., 2008, 73, 6841-6844.

DOI: 10.1021/jo801191v (free Supporting Information)


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Abstract

A number of alkynyl pinacolboronates were stereoselectively reduced to the cis-alkenyl pinacolboronates via hydroboration with dicyclohexylborane followed by chemoselective protodeboronation using acetic acid. Treatment with potassium hydrogen fluoride smoothly converted these to the corresponding potassium organotrifluoroborates.


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Key Words

Reduction of Alkynes, Hydroboration, Vinylboronates


ID: J42-Y2008-2430