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Cobalt-Catalyzed Regioselective Carboamidation of Alkynes with Imides Enabled by Cleavage of C–N and C–C Bonds

Xiang‐Ting Min, Ding‐Wei Ji, Hao Zheng, Bingzhi Chen, Yan‐Cheng Hu, Boshun Wan, Qing‐An Chen

2020Organic Letters28 citationsDOI

Abstract

Through the oxidative addition of cobalt into the N-C(O) bond of phthalimide and the subsequent decarbonylation, we describe an efficient cobalt-catalyzed intermolecular decarbonylative carboamidation of alkynes. High regioselectivities have been achieved for unsymmetrical alkynes (including aryl-alkyl or aryl-aryl) to deliver polysubstituted isoquinolones. To facilitate step economy, a three-component decarbonylative carboamidation of alkynes with phthalic anhydrides and amines has been demonstrated using the current cobalt catalysis.

Topics & Concepts

ChemistryRegioselectivityCatalysisCobaltCleavage (geology)Bond cleavageCombinatorial chemistryMedicinal chemistryStereochemistryPolymer chemistryOrganic chemistryFracture (geology)EngineeringGeotechnical engineeringCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesSynthesis and Catalytic Reactions
Cobalt-Catalyzed Regioselective Carboamidation of Alkynes with Imides Enabled by Cleavage of C–N and C–C Bonds | Litcius