Synthesis of 2-Formyl Carbazoles via Tandem Reaction of Indolyl Nitrones with 2-Methylidene Cyclic Carbonate
Sujin Min, Taeeun Kim, Taejoo Jeong, Jun‐Hyeok Yang, Yebin Oh, Kyeongwon Moon, Amitava Rakshit, In Su Kim
Abstract
The synthesis of functionalized carbazoles as privileged nitrogen heterocycles has emerged as a central topic in drug discovery and material science. We herein disclose the rhodium(III)-catalyzed cross-coupling reaction between indolyl nitrones and 2-methylidene cyclic carbonate as an allylating surrogate, resulting in the formation of C2-formylated carbazoles via tandem C-H allylation, [3 + 2] cycloaddition, aromatization, and benzylic oxidation. The synthetic utility of this protocol is highlighted by a variety of post-transformations of C2-formylated carbazoles.
Topics & Concepts
ChemistryCycloadditionAromatizationTandemCombinatorial chemistryRhodiumCatalysisOrganic chemistryStereochemistryMaterials scienceComposite materialCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsSynthesis of Indole Derivatives