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镍催化的1,3-烯炔与烷基溴的三组分串联自由基环化1,5-双官能化反应

Nickel-Catalyzed Three-Component Tandem Radical Cyclization 1,5-Difunctionalization of 1,3-Enynes and Alkyl Bromide.

作者信息

Li Ming, Sun Guo-Qing, Liu Yu-Yu, Li Shun-Xi, Liu Hai-Chao, Qiu Yi-Feng, Chen Dong-Pin, Wang Xi-Cun, Liang Yong-Min, Quan Zheng-Jun

机构信息

College of Chemistry and Chemical Engineering, Gansu International Scientific and Technological Cooperation Base of Water-Retention Chemical Functional Materials, Northwest Normal University, Lanzhou, Gansu 730070, China.

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China.

出版信息

J Org Chem. 2023 Feb 3;88(3):1403-1410. doi: 10.1021/acs.joc.2c02271. Epub 2023 Jan 19.

Abstract

A nickel-catalyzed three-component tandem radical cyclization reaction of aryl bromides with 1,3-enynes and aryl boric acids to construct γ-lactam-substituted allene derivatives has been described. This protocol provides lactam alkyl radicals through the free radical cyclization process, which can be effectively used to participate in the subsequent multicomponent coupling reaction so that 1,3-enynes could directly convert into corresponding poly-substituted allene compounds. In addition, this efficient method enjoys a broad substrate scope and provides a series of 1,5-difunctionalized allenes in a one-pot reaction.

摘要

已报道了一种镍催化的芳基溴化物与1,3-烯炔和芳基硼酸的三组分串联自由基环化反应,用于构建γ-内酰胺取代的丙二烯衍生物。该方法通过自由基环化过程提供内酰胺烷基自由基,其可有效地用于参与随后的多组分偶联反应,从而使1,3-烯炔能够直接转化为相应的多取代丙二烯化合物。此外,这种高效方法具有广泛的底物范围,并能在一锅反应中提供一系列1,5-二官能化的丙二烯。

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