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- Title
Conversion of anilines to chiral benzylic amines via formal one-carbon insertion into aromatic C–N bonds.
- Authors
Li, Lei; Yang, Min; He, Qiuqin; Fan, Renhua
- 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. Atom insertion into aromatic carbon-nitrogen (C-N) bonds is useful for the synthesis of nitrogen-containing molecules, but challenging due to the inert nature of these bonds. Here, the authors report one-carbon insertion into aromatic C-N bonds to directly convert anilines to chiral benzylic amines.
- Subjects
ANILINE; AMINES; AZIRIDINATION; AROMATIC amines; AROMATICITY; SULFUR
- Publication
Nature Communications, 2020, Vol 11, Issue 1, pN.PAG
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-020-18593-4