Cobalt-Catalyzed Thioamide Directed C(arene)–H Annulation with Ynamide: Regioselective Access to 2-Amidoindenones
Somratan Sau, Arghadip Ghosh, Majji Shankar, Manash Protim Gogoi, Akhila K. Sahoo
Abstract
Demonstrated herein is an unprecedented thioamide-directed cobalt (Co)-catalyzed umpolung annulation of sulfoximines enabled aryl thioamide with ynamide for the synthesis of highly substituted 2-amidoindenones. The cyclization is regioselective, making β-C-C and α-C-CO bonds. The transformation is even successful on a gram scale, exhibiting broad scope with labile functional group tolerance and constructing 43 unusual 2-amidoindenones of structural diversity. Control experiments and mechanistic investigation validate the regioselectivity outcome in this transformation.
Topics & Concepts
ChemistryThioamideRegioselectivityUmpolungAnnulationCatalysisCombinatorial chemistryCobaltFunctional groupArylStereochemistryOrganic chemistryMedicinal chemistryAlkylPolymerNucleophileCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques