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Nickel-Catalyzed Formal Aminocarbonylation of Secondary Benzyl Chlorides with Isocyanides

Yun Wang, Wenyi Huang, Chenglong Wang, Jingping Qü, Yifeng Chen

2020Organic Letters29 citationsDOI

Abstract

Phenylacetamides represent versatile feedstocks in synthetic chemistry, widely existing in drug molecules and natural products. Herein, we disclose a nickel-catalyzed formal aminocarbonylation of secondary benzyl chlorides with isocyanides yielding α-substituted phenylacetamide with steric hindrance, which is synthetically challenging via palladium-catalyzed aminocarbonylation. The reaction features wide functional group tolerance under mild conditions, highlighted by the tolerance of various aromatic halide (-Cl, -Br, -I) and heteroaromatic rings (pyridine and pyrazine).

Topics & Concepts

ChemistryCatalysisNickelCombinatorial chemistryOrganic chemistryCatalytic C–H Functionalization MethodsChemical Synthesis and ReactionsCatalytic Cross-Coupling Reactions
Nickel-Catalyzed Formal Aminocarbonylation of Secondary Benzyl Chlorides with Isocyanides | Litcius