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

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 ?-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.

SUBMITTER: Li L

PROVIDER: S-EPMC7511326 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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

Li Lei L Yang Min M He Qiuqin Q Fan Renhua R

Nature communications 20200923 1

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 d ...[more]

PMID: 32968063

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