Journal of the American Chemical Society 2006-10-04

Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids: two distinct C-H activation pathways.

Xiao Chen, Charles E Goodhue, Jin-Quan Yu

Index: J. Am. Chem. Soc. 128 , 12634, (2006)

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Abstract

Palladium-catalyzed alkylations of sp2 and sp3 C-H bonds with either methylboroxine or alkylboronic acids were developed. Ag2O or AgCO3 is used as a crucial oxidant and promoter for the transmetalation step. Ether, ester, alcohol, and alkene functional groups are tolerated. A new C-H activation pathway differing from the cyclometalation process is elucidated using methylboroxine as the coupling partner.