Copper-Catalyzed Boron-Selective C(sp²)-C(sp³) Oxidative Cross-Coupling of Arylboronic Acids and Alkyltrifluoroborates Involving a Single-Electron Transmetalation Process

A rapid and highly selective oxidative cross-coupling reaction between readily available and shelf-stable arylboronic acids and primary or secondary potassium alkyltrifluoroborates was devised and developed, which works under mild conditions using copper(II) acetate as the catalyst and silver oxide as the oxidant. Initial experimental results indicate that a single-electron transmetalation process is involved. This approach effectively bypasses the problems associated with the traditional cross-coupling reactions of alkylboronates and thus provides a complementary method in building C(sp²)-C(sp³) bonds.