Ligand-promoted cobalt-catalyzed radical hydroamination of alkenes

Xuzhong Shen, Xu Chen, Jieping Chen, Yufeng Sun, Zhaoyang Cheng and Zhan Lu ()
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Xuzhong Shen: Zhejiang University
Xu Chen: Zhejiang University
Jieping Chen: Zhejiang University
Yufeng Sun: Zhejiang University
Zhaoyang Cheng: Zhejiang University
Zhan Lu: Zhejiang University

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: Abstract Highly regio- and enantioselective intermolecular hydroamination of alkenes is a challenging process potentially leading to valuable chiral amines. Hydroamination of alkenes via metal-catalyzed hydrogen atom transfer (HAT) with good regioselectivity and functional group tolerance has been reported, however, high enantioselectivity has not been achieved due to the lack of suitable ligands. Here we report a ligand-promoted cobalt-catalyzed Markovnikov-type selective radical hydroamination of alkenes with diazo compounds. This operationally simple protocol uses unsymmetric NNN-tridentate (UNT) ligand, readily available alkenes and hydrosilanes to construct hydrazones with good functional group tolerance. The hydrazones can undergo nitrogen–nitrogen bond cleavage smoothly to deliver valuable amine derivatives. Additionally, asymmetric intermolecular hydroamination of unactivated aliphatic terminal alkenes using chiral N-imidazolinylphenyl 8-aminoquinoline (IPAQ) ligands has also been achieved to afford chiral amine derivatives with good enantioselectivities.

Date: 2020
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DOI: 10.1038/s41467-020-14459-x

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