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

Leipeng Xie, Shenghao Wang, Lanlan Zhang, Lei Zhao, Chun Luo, Linping Mu, Xiuguang Wang and Chao Wang ()
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Leipeng Xie: Tianjin Normal University
Shenghao Wang: Tianjin Normal University
Lanlan Zhang: Tianjin Normal University
Lei Zhao: Tianjin Normal University
Chun Luo: Tianjin Normal University
Linping Mu: Tianjin Normal University
Xiuguang Wang: Tianjin Normal University
Chao Wang: Tianjin Normal University

Nature Communications, 2021, vol. 12, issue 1, 1-10

Abstract: 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.

Date: 2021
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DOI: 10.1038/s41467-021-26527-x

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