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

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, β-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 β-hydride elimination, while the fluoride serves to activate the tin reagent for efficient transmetalation. Copyright © 2003 American Chemical Society.