Configuration Retention in P-Trifluoromethyl Phosphine Enabled Rh(I)-Catalyzed Decarbonylative Coupling of Carboxylates and Boroxines

Abstract

As compared with asymmetric catalysis, the memory of chirality provides another promising strategy to introduce chiral centers in light of numerous chiral starting materials that can be accessed. Decarboxylative coupling has become an important strategy for C–C or C–X bond formation over decades of development for its versatility and the low cost and structural diversity of carboxylic acids. However, the memory of chirality or more general configuration retention in this transformation has seldom been studied. Here, we report a novel π acceptor-type ligand P-trifluoromethyl phosphine enabled Rh(I)-catalyzed decarbonylative coupling of carboxylates and boroxines. The configuration of the α-carbon can be fully retained in this transformation for chiral, cis-, or trans-substrates. Several P-trifluoromethyl phosphine-Rh(I) carbonyl complexes were prepared and their v(CO) values were compared with known complexes, which indicated that the π-accepting property of the ligand is important to the decarbonylative reaction.