铜催化1,3-二烯的三组分碳官能化反应

IF 13.1 1区 化学 Q1 CHEMISTRY, PHYSICAL
Vincent R. Viviani, Travis L. Buchanan, An Thien Ho, John A. Little, Andrei G. Popov, Matthew Barnett, Kira Q. McMahon, Samuel N. Gockel, Kami L. Hull
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引用次数: 0

摘要

1,3-二烯的碳胺化以一种步骤经济的方式提供了直接和有效的烯丙胺获取途径。在此,我们公开了一种三组分1,3-二烯碳胺化反应,该反应提供了对多种烯丙基胺的模块化访问。具有代表性的1,3-二烯,活化的烷基卤化物和胺被证明可以作为该反应的组分,收率从高达96%不等。在1,2-或1,4-碳胺化反应中,取代和未取代的二烯衍生物的区域异构体比例都很高(≥12:1)。机理研究表明,反应是通过原子转移自由基加成二烯进行的,产生了可分离的烯丙基卤化物中间体。范围扩展到一般的碳官能化,通过在形成烯丙基卤化物的反应中加入外源的O, S, P或C亲核试剂和碱,在两步,一锅过程中。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Cu-Catalyzed Three-Component Carbofunctionalization of 1,3-Dienes

Cu-Catalyzed Three-Component Carbofunctionalization of 1,3-Dienes
The carboamination of 1,3-dienes provides direct and efficient access to allylic amines in a step-economical fashion. Herein, we disclose a three-component 1,3-diene carboamination reaction that provides modular access to a multitude of allylic amines. A representative scope of 1,3-dienes, activated alkyl halides, and amines is demonstrated to serve as components for this reaction, with yields ranging from up to 96%. High regioisomeric ratios are observed with both substituted and unsubstituted diene derivatives for either 1,2- or 1,4-carboamination (≥12:1). Mechanistic investigations demonstrate that the reaction proceeds via atom transfer radical addition to the diene, affording an isolable allylic halide intermediate. The scope was expanded to a general carbofunctionalization, by adding an exogenous O, S, P, or C nucleophile and base to the reaction upon formation of the allylic halide, in a two-step, one-pot process.
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来源期刊
ACS Catalysis
ACS Catalysis CHEMISTRY, PHYSICAL-
CiteScore
20.80
自引率
6.20%
发文量
1253
审稿时长
1.5 months
期刊介绍: ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.
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