The First Suzuki Cross-Couplings of Aryltrimethylammonium Salts

The first Suzuki cross-coupling reaction of aryltrimethylammonium triflates based on the use of an IMes.Ni(0) catalyst system is described. A wide range of electron-withdrawing and electron-donating substituents are tolerated on both the aryltrimethylammonium triflate and the boronic acid components of this reaction. In addition to arylboronic acids, the scope of the reaction is extended to encompass both boronate esters and alkenylboranes. This methodology constitutes a novel, mild method to activate anilines for metal-catalyzed cross-coupling reactions.