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Synthesis of Isocyanides by Reacting Primary Amines with Difluorocarbene

Yi-Xin Si, Peng-Fei Zhu and Song-Lin Zhang*

*Key Laboratory of Synthetic and Biological Colloids, School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu 214122, China, Email:

Y.-X. Si, P.-F. Zhu, S.-L. Zhang, Org. Lett., 2020, 22, 9086-9090.

DOI: 10.1021/acs.orglett.0c03472 (free Supporting Information)

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Difluorocarbene, generated in situ from chlorodifluoroacetate via decarboxylation, reacts efficiently with primary amines to produce isocyanides. Various primary amines can be converted, including aryl, heteroaryl, benzyl, and alkyl amines, as well as amine residues in amino acids and peptides. Late-stage functionalization of biologically active amines is also demonstrated.

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Key Words


ID: J54-Y2020