Divergent Synthesis of Tetrasubstituted Phenols via [3 + 3] Cycloaddition Reaction of Vinyl Sulfoxonnium Ylides with Cyclopropenones
Shaoyong Chen, Yao‐Fu Zeng, Wen‐Xuan Zou, Dan‐Ting Shen, Yi‐Chuan Zheng, Jia‐Lin Song, Shang‐Shi Zhang
Abstract
Two categories of tetrasubstituted phenols were prepared via the cycloaddition reaction of vinyl sulfoxonnium ylides with cyclopropenones in a switchable manner. Copper carbenoid was proposed as the active intermediate in the process of 2,3,4,5-tetrasubstituted phenols formation, while 2,3,5,6-tetrasubstituted phenols were generated via the direct [3 + 3] annulation of vinyl sulfoxonnium ylides with cyclopropenones under metal-free conditions. Further synthetic applications were also demonstrated.
Topics & Concepts
ChemistryPhenolsCycloadditionCarbenoidAnnulationOrganic chemistryReaction conditionsCombinatorial chemistryCatalysisRhodiumCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions