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

Lei Li, Min Yang, Qiuqin He and Renhua Fan ()
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Lei Li: Fudan University
Min Yang: Gannan Medical University
Qiuqin He: Fudan University
Renhua Fan: Fudan University

Nature Communications, 2020, vol. 11, issue 1, 1-9

Abstract: 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.

Date: 2020
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DOI: 10.1038/s41467-020-18593-4

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