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Intramolecular Csp³-H/C-C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines.

ABSTRACT: The intramolecular Csp³-H and/or C-C bond amination is very important in modern organic synthesis due to its efficiency in the construction of diversified N-heterocycles. Herein, we report a novel intramolecular cyclization of alkyl azides for the synthesis of cyclic imines and tertiary amines through selective Csp³-H and/or C-C bond cleavage. Two C-N single bonds or a C[double bond, length as m-dash]N double bond are efficiently constructed in these transformations. The carbocation mechanism differs from the reported metal nitrene intermediates and therefore enables metal-free and new transformation.

SUBMITTER: Wen X

PROVIDER: S-EPMC8159442 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Intramolecular Csp3-H/C-C bond amination of alkyl azides for the selective synthesis of cyclic imines and tertiary amines.

Wen Xiaojin X Li Xinyao X Luo Xiao X Wang Weijin W Song Song S Jiao Ning N

Chemical science 20200407 17

The intramolecular Csp3-H and/or C-C bond amination is very important in modern organic synthesis due to its efficiency in the construction of diversified N-heterocycles. Herein, we report a novel intramolecular cyclization of alkyl azides for the synthesis of cyclic imines and tertiary amines through selective Csp3-H and/or C-C bond cleavage. Two C-N single bonds or a C[double bond, length as m-dash]N double bond are efficiently constructed in these transformations. The ca ...[more]

PMID: 34122906

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