Sulfilimines as Transformable and Retainable Directing Groups in Rhodium-Catalyzed <i>ortho</i>-C–H Bond Functionalization
Jiechun Liu, Xiaoyan Jia, Liangbin Huang
Abstract
Shown herein is the first time that the sulfilimine is utilized as a directing group for Rh(III)-catalyzed C–H activation/annulation with intermolecular and intramolecular alkyne compounds. Sulfilimine serves as a transformable directing group, an internal oxidant, in the annulation with an alkyne moiety via N–S bond cleavage. Notably, the retention of sulfilimine as a directing group is also achieved in the Rh(III)-catalyzed ortho-alkynylation with alkyne bromides.
Topics & Concepts
AnnulationChemistryAlkyneIntramolecular forceMoietyRhodiumCatalysisSurface modificationAlkynylationBond cleavageMedicinal chemistryIntermolecular forceCleavage (geology)StereochemistryOrganic chemistryMoleculePhysical chemistryGeotechnical engineeringFracture (geology)EngineeringCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCatalytic Alkyne Reactions