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Preparation of (E)-1-Alkenylboronic Acid Pinacol Esters via Transfer of Alkenyl Group from Boron to Boron

Kazuya Shirakawa, Akira Arase, Masayuki Hoshi*

*Department of Applied and Environmental Chemistry, Kitami Institute of Technology, 165 Koen-cho, Kitami, Hokkaido 090-8507, Japan Email:

K. Shirakawa, A. Arase, M. Hoshi, Synthesis, 2004, 1814-1820.

DOI: 10.1055/s-2004-829165

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A mild hydroboration of various 1-alkynes with pinacolborane was achieved in the presence of a catalytic amount of dicyclohexylborane at room temperature under neat conditions to afford the corresponding (E)-1-alkenylboronic acid pinacol esters in good yields.

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proposed catalytic cycle

Key Words

(E)-1-alkenylboronic acid pinacol ester, 1-alkyne, dicyclohexylborane, catecholborane, pinacolborane, hydroboration

ID: J66-Y2004-2220