Methylpentanediolborane:  Easy Access to New Air- and Chromatography-Stable, Highly Functionalized Vinylboronates

Nageswaran PraveenGanesh, Sylvain d'Hondt, and Pierre Yves Chavant*
Dpartement de Chimie Molculaire, CNRS, Universit Joseph Fourier, BP-53, 38041 Grenoble Cedex 9, France
J. Org. Chem., 2007, 72 (12), pp 4510–4514
DOI: 10.1021/jo070504g
Publication Date (Web): May 11, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, Pierre-Yves.Chavant@ujf-grenoble.fr

Abstract

Abstract Image

Methylpentanediolborane (MPBH) 1 can be prepared easily by reaction of hexyleneglycol with BH3/DMS or B2H6 generated from NaBH4 and I2. MPBH hydroborates stereo- and regioselectively highly functionalized alkynes, including propargyl bromide and propionaldehyde acetal. MPBH compares favorably with pinacolborane in terms of reactivity. The obtained vinylboronic esters are air- and chromatography-stable.

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History

  • Published In Issue June 08, 2007
  • Received March 16, 2007

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