Ylide‐Functionalized Diisopropyl Phosphine (prYPhos): A Ligand for Selective Suzuki‐Miyaura Couplings of Aryl Chlorides

Abstract

Abstract The ylide‐functionalized diisopropyl phosphine (prYPhos) promotes Pd‐catalyzed Suzuki‐Miyaura couplings of aryl chlorides and bromides with arylboronic acids. Using Pd 2 (dba) 3 /prYPhos as the catalyst and K 2 CO 3 as the base, various (hetero)biaryls were synthesized in 45–98% yields at mild reaction conditions, tolerating sensitive functional groups and steric hindrance. The electron rich, sterically demanding ligand induces a high selectivity for halides versus triflate. Chloroaryl triflates were selectively coupled at the chloride, leaving inherently more reactive triflate groups in place. magnified image