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Aldehyde as a Traceless Directing Group for Regioselective C–H Alkylation Catalyzed by Rhodium(III) in Air

Si-Qi Chen, Xinran Li, Chao‐Jun Li, Juan Fan, Zhong‐Wen Liu, Xian‐Ying Shi

2020Organic Letters25 citationsDOI

Abstract

The aromatic aldehyde as a traceless directing group for the regionselective C-H alkylation catalyzed by rhodium(III) under aerobic atmospheric conditions has been developed. The process involves an aldehyde assisted direct addition of C-H bond to unsaturated electrophiles of acrylates or acrylic acids, and the subsequent decarbonylation. A trace amount of water is found to favor the reaction.

Topics & Concepts

ChemistryRhodiumAldehydeElectrophileDecarbonylationRegioselectivityAlkylationCatalysisMedicinal chemistryOrganic chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsCatalytic Cross-Coupling Reactions
Aldehyde as a Traceless Directing Group for Regioselective C–H Alkylation Catalyzed by Rhodium(III) in Air | Litcius