Ni(II)-catalyzed asymmetric alkenylation and arylation of aryl ketones with organoborons via 1,5-metalate shift

Haipeng Wei, Yicong Luo, Jinbao Ren, Qianjia Yuan () and Wanbin Zhang ()
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Haipeng Wei: Shanghai Jiao Tong University
Yicong Luo: Shanghai Jiao Tong University
Jinbao Ren: Shanghai Jiao Tong University
Qianjia Yuan: Shanghai Jiao Tong University
Wanbin Zhang: Shanghai Jiao Tong University

Nature Communications, 2024, vol. 15, issue 1, 1-10

Abstract: Abstract Chiral tertiary alcohols are an important structural motif, however, the general and efficient methodologies for their synthesis are less reported. Herein, we report a Ni(ІІ)-catalyzed asymmetric alkenylation and arylation of aryl ketones with organoborons under air via a 1,5-metalate shift strategy to obtain chiral tertiary allylic alcohols and diaryl alcohols. The reaction demonstrates good functional group tolerance and delivers chiral tertiary alcohols with good to excellent results. Furthermore, this method can be applied to the late-stage modification of drugs and the efficient synthesis of natural products. Notably, the reaction proceeds through an outer-sphere mechanism. The Ni(II) complex functions both as a Lewis acid to activate the ketone and create a chiral environment, and as coordination bridge linking the ketone and the organoboron-derived “ate” complex, facilitating the 1,5-metalate shift without forming a C-Ni bond. This approach contrasts with traditional transition metal-catalyzed nucleophilic addition reactions that involve carbon-metal bond formation.

Date: 2024
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DOI: 10.1038/s41467-024-53005-x

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