Journal of the American Chemical Society 2003-04-02

Room-temperature Stille cross-couplings of alkenyltin reagents and functionalized alkyl bromides that possess beta hydrogens.

Karsten Menzel, Gregory C Fu

Index: J. Am. Chem. Soc. 125 , 3718, (2003)

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Abstract

This communication describes a significant expansion in the scope of Stille reactions of Csp3-X electrophiles, specifically, that Pd/P(t-Bu)2Me catalyzes the room-temperature cross-coupling of a variety of functionalized, beta-hydrogen-containing alkyl bromides with an array of alkenyltin reagents. The structure of the phosphine (P(t-Bu)2Me) is well suited for facilitating oxidative addition and avoiding beta-hydride elimination, while the fluoride serves to activate the tin reagent for efficient transmetalation.