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Directed nickel-catalyzed regio- and diastereoselective arylamination of unactivated alkenes.

ABSTRACT: Few methods have been reported for intermolecular arylamination of alkenes, which could provide direct access to important arylethylamine scaffolds. Herein, we report an intermolecular syn-1,2-arylamination of unactivated alkenes with arylboronic acids and O-benzoylhydroxylamine electrophiles with Ni(II) catalyst. The cleavable bidentate picolinamide directing group facilitates formation of stabilized 4-, 5- or 6-membered nickelacycles and enables the difunctionalization of diverse alkenyl amines with high levels of regio-, chemo- and diastereocontrol. This general and practical protocol is compatible with broad substrate scope and high functional group tolerance. The utility of this method is further demonstrated by the site-selective modification of pharmaceutical agents.

SUBMITTER: Xie L

PROVIDER: S-EPMC8560905 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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Directed nickel-catalyzed regio- and diastereoselective arylamination of unactivated alkenes.

Xie Leipeng L Wang Shenghao S Zhang Lanlan L Zhao Lei L Luo Chun C Mu Linping L Wang Xiuguang X Wang Chao C

Nature communications 20211101 1

Few methods have been reported for intermolecular arylamination of alkenes, which could provide direct access to important arylethylamine scaffolds. Herein, we report an intermolecular syn-1,2-arylamination of unactivated alkenes with arylboronic acids and O-benzoylhydroxylamine electrophiles with Ni(II) catalyst. The cleavable bidentate picolinamide directing group facilitates formation of stabilized 4-, 5- or 6-membered nickelacycles and enables the difunctionalization of diverse alkenyl amine ...[more]

PMID: 34725344

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