Modulating Lewis acidity with boronamides and boronates: effect on behavior in borylation and cross-coupling

Abstract

Modulation of boron-Lewis acidities with cyclic boronamide and boronate moieties, which decisively affects the regiochemical outcome of the copper-catalyzed hydroboration of terminal alkynes, is described. The direct Suzuki–Miyaura coupling of strongly Lewis acidity-diminished R–B(dan), previously believed to be inert toward the reaction, is also reported.