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Nickel-Catalyzed Reductive Cross-Coupling of <i>N</i>-Acyl and <i>N</i>-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides

Erdong Qu, Shangzhang Li, Jin Bai, Yan Zheng, Wanfang Li

2021Organic Letters28 citationsDOI

Abstract

Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.

Topics & Concepts

ChemistrySulfonylNitroCatalysisArylReductive eliminationAlkylNickelSubstrate (aquarium)Combinatorial chemistryCoupling reactionOrganic chemistryMedicinal chemistryGeologyOceanographyAdvanced Synthetic Organic ChemistryCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis
Nickel-Catalyzed Reductive Cross-Coupling of <i>N</i>-Acyl and <i>N</i>-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides | Litcius