Ni-Catalyzed 1,1- and 1,3-Aminoboration of Unactivated Alkenes

Alkene borylfunctionalization reactions have emerged as useful methods for chemical synthesis. While much progress has been made on 1,2-borylamination reactions, the related 1,1- and 1,3-borylaminations have not been reported. Herein, a Ni-catalyzed 1,1-borylamination of 1,1-disubstituted and monosu...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2023-12, Vol.145 (50), p.27254-27261
Main Authors: Lyu, Mao-Yun, Morais, Gabriel N., Chen, Shuming, Brown, M. Kevin
Format: Article
Language:English
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Summary:Alkene borylfunctionalization reactions have emerged as useful methods for chemical synthesis. While much progress has been made on 1,2-borylamination reactions, the related 1,1- and 1,3-borylaminations have not been reported. Herein, a Ni-catalyzed 1,1-borylamination of 1,1-disubstituted and monosubstituted alkenes and a 1,3-borylamination of cyclic alkenes are presented. Key to development of these reactions was the identification of an alkyllithium activator in combination with Mg salts. The utility of the products and the mechanistic details are discussed.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.3c12770