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Generation of Cations from Alkoxides: Allylation of Propargyl Alcohols

George W. Kabalka,* Min-Liang Yao and Scott Borella

*Departments of Chemistry and Radiology, The University of Tennessee, Knoxville, Tennessee 37996-1600, Email:

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

DOI: 10.1021/ja061379d (free Supporting Information)

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The reaction of alkoxides with boron trichloride results in the generation of cations that can be allylated in subsequent transformations. The absence of Brønsted acids can make a significant difference in such syntheses.

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Titanium(IV) Halide Mediated Coupling of Alkoxides and Alkynes: An Efficient and Stereoselective Route to Trisubstituted (E)-Alkenyl Halides

M.-L. Yao, T. R. Quick, Z. Wu, M. P. Quinn, G. W. Kabalka, Org. Lett., 2009, 11, 2647-2649.

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

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

Key Words

Propargylic Alcohols, Benzylic Alcohols, Alkynes, Allylation, Benzylic Substitution, Hosomi-Sakurai Reaction

ID: J48-Y2006-2750