Rh(<scp>iii</scp>)-Catalyzed sequential <i>ortho</i>-C–H oxidative arylation/cyclization of sulfoxonium ylides with quinones toward 2-hydroxy-dibenzo[<i>b,d</i>]pyran-6-ones
Yaqun Dong, Jin‐Tao Yu, Song Sun, Jiang Cheng
Abstract
A rhodium(iii)-catalyzed ortho-C-H functionalization of sulfoxonium ylides followed by intramolecular annulation reactions with quinones was described, where the carbonyl in sulfoxonium ylides served as a chelation group. This protocol leads to the efficient formation of 2-hydroxy-6H-benzo[c]chromen-6-one derivatives, proceeding with the cleavage of the C(O)-S bond in sulfoxonium ylides. This protocol featured high chemo-selectivity and functional group tolerance, where sulfoxonium ylides acted as the aroyl sources.
Topics & Concepts
ChemistryAnnulationIntramolecular forcePyranCatalysisRhodiumStereochemistryCleavage (geology)Bond cleavageMedicinal chemistrySurface modificationCombinatorial chemistryOrganic chemistryPhysical chemistryGeotechnical engineeringFracture (geology)EngineeringCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesSynthesis and Catalytic Reactions