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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Nickel-Catalyzed Umpolung Allylation of Imines with Allylic Alcohols
Kuo Yuan1, Xin Xie2, Qiting Wu3
1Henan Institute of Advanced Technology, Zhengzhou University, 100 Science Avenue, Zhengzhou 450001, China.
Abstract:
A nickel-catalyzed allylation of imines, including cyclic imines such as dibenzoxazepines, quinazolinones, and quinoxalin-2(1H)-ones and linear imines, using allylic alcohols as pro-nucleophiles has been developed. This transformation affords homoallylic amines in good to excellent yields with high levels of regio- and diastereoselectivity. Mechanistic studies suggest that the bis(π-allyl)nickel(II) intermediate serves as a crucial intermediate in the catalytic cycle, exhibiting nucleophilic reactivity through its η1,η3 coordination mode.
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