Substitution of Hydroxyl Groups with Alkynyl Moieties Using Alkynylboron Dihalides:  An Efficient Approach to Secondary Alkylacetylene Derivatives

George W. Kabalka,* Min-Liang Yao, and Scott Borella
Departments of Chemistry and Radiology, The University of Tennessee, Knoxville, Tennessee 37996-1600
Org. Lett., 2006, 8 (5), pp 879–881
DOI: 10.1021/ol052957i
Publication Date (Web): February 4, 2006
Copyright © 2006 American Chemical Society
*

 To whom all correspondence should be addressed. Phone:  (865) 974-2160. Fax:  (865) 974-2297.

, kabalka@utk.edu

Abstract

Abstract Image

The reaction of alkynylboron dihalides with benzylic, allylic, and propargylic alcohols provides an efficient route to internal acetylenes. Isomerization of the product alkynes does not occur under the reaction conditions.

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History

  • Published In Issue March 02, 2006
  • Received December 6, 2005

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