Enantioselective Synthesis of Triarylmethanes via Intermolecular C–H Functionalization of Cyclohexadienes with Diaryldiazomethanes
Maizie Lee, Huw M. L. Davies
Abstract
High Resolution Image Download MS PowerPoint Slide Rhodium-catalyzed C–H functionalization of cyclohexadiene derivatives with diaryldiazomethanes followed by oxidation with DDQ provides ready access to triarylmethanes. Two chiral dirhodium tetracarboxylates, Rh 2 ( S -PTAD) 4 and Rh 2 ( S -TPPTTL) 4, were found to be the optimum chiral catalysts for these transformations. This method showcases the ability of diaryldiazomethanes to perform intermolecular C–H insertion with high enantioselectivity and good yields. The method has a broad substrate scope, leading to triarylmethane products with a variety of aryl and heteroaryl substituents, including benzofuran and pyridine heterocycles.
Topics & Concepts
ChemistryEnantioselective synthesisIntermolecular forceCatalysisSurface modificationRhodiumBenzofuranArylPyridineCombinatorial chemistrySubstrate (aquarium)Organic chemistryMoleculeGeologyAlkylPhysical chemistryOceanographyCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions