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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, Email: kabalkautk.edu

G. W. Kabalka, M.-L. Yao, S. Borella, Org. Lett., 2006, 8, 879-881.

DOI: 10.1021/ol052957i (free Supporting Information)


Abstract

The reaction of alkynylboron dihalides with benzylic, allylic, and propargylic alcohols provides an efficient route to internal acetylenes without isomerization of the product alkynes under the reaction conditions.

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Generation of Cations from Alkoxides: Allylation of Propargyl Alcohols

G. W. Kabalka, M.-L. Yao, S. Borella, J. Am. Chem. Soc., 2006, 128, 11320-11321.


Key Words

Substituted Alkynes, Benzylation


ID: J54-Y2006-650