Palladium-Catalyzed Cross-Coupling of Organoboron Compounds with Iodonium Salts and Iodanes

Abstract

The palladium-catalyzed cross-coupling reaction of iodinanes (iodonium salts and iodanes) with organoboron compounds to form carbon−carbon bonds was achieved at ambient temperature under aqueous conditions in the absence of base. Coupling of phenylboronic acid with diphenyliodonium tetrafluoroborate in the presence of Pd(PPh₃)₄ (0.2 mol %) or Pd(OAc)₂ (0.2 mol %) under aqueous conditions gave biphenyl in almost quantitative yield. Under the same conditions, substituted boronic acids, boronates, and trialkylboranes were readily coupled with diaryl-, alkenyl-, and alkynyliodonium salts. Finally, the iodanes ArI(OH)OTs underwent cross-coupling with boronic acids, boronates, and trialkylboranes to afford biphenyls and aryl-substituted alkenes.