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: kabalkautk.edu
G. W. Kabalka, M.-L. Yao, S. Borella, J. Am. Chem. Soc., 2006, 128, 11320-11321.
DOI: 10.1021/ja061379d (free Supporting Information)
see article for more reactions
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.
see article for more examples
M.-L. Yao, T. R. Quick, Z. Wu, M. P. Quinn, G. W. Kabalka, Org. Lett., 2009, 11, 2647-2649.
G. W. Kabalka, M.-L. Yao, S. Borella, Org. Lett., 2006, 8, 879-881.