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Conversion of anilines to chiral benzylic amines via formal one-carbon insertion into aromatic C–N bonds

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  • Lei Li

    (Fudan University)

  • Min Yang

    (Gannan Medical University)

  • Qiuqin He

    (Fudan University)

  • Renhua Fan

    (Fudan University)

Abstract

Insertion of atoms into aromatic carbon-nitrogen bonds is an appealing method for the synthesis of nitrogen-containing molecules and it has the advantage of the availability and abundance of anilines. However, the direct cleavage of aromatic carbon-nitrogen bonds is challenging due to the particularly inert and stable nature of these bonds. Here we report a formal, enantioselective one-carbon insertion into an aromatic carbon-nitrogen bond via an aromaticity dissembly-reconstruction process to directly convert anilines to chiral α-branched benzylic amines. The process involves oxidative dearomatization of para-substituted anilines, chiral sulfur ylide-mediated asymmetric aziridination, and subsequent rearrangement. Chiral sulfur ylides serve as one-carbon insertion units.

Suggested Citation

  • Lei Li & Min Yang & Qiuqin He & Renhua Fan, 2020. "Conversion of anilines to chiral benzylic amines via formal one-carbon insertion into aromatic C–N bonds," Nature Communications, Nature, vol. 11(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-18593-4
    DOI: 10.1038/s41467-020-18593-4
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