Enantioselective Synthesis of Triarylmethanes via Palladium-Catalyzed Desymmetric Carbonylation of Cyclic Diaryliodonium Salts

A highly enantioselective desymmetric strategy was developed for the synthesis of enantioenriched triarylmethanes via palladium-catalyzed carbonylation reactions of six-membered cyclic diaryliodonium salts with CO gas and alcohols/amines. This methodology demonstrated wide substrate generality and functional group compatibility under mild conditions. Comprehensive kinetic studies and nonlinear effect studies were conducted to elucidate the reaction mechanism. Notably, obviously different <i>in vitro</i> anti-inflammatory performances on inhibition of NO production were observed for two enantiomers of selected triarylmethanes, highlighting the necessity for pharmacological evaluation of a single stereoisomer in drug development.