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Nickel-Catalyzed Formal Aminocarbonylation of Secondary Benzyl Chlorides with Isocyanides
Yun Wang1, Wenyi Huang1, Chenglong Wang1
1Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology 130 Meilong Road, Shanghai 200237, China.
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).
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