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含氮杂芳烃与卤代烃的一般电化学Minisci烷基化反应。

General electrochemical Minisci alkylation of -heteroarenes with alkyl halides.

作者信息

Del Río-Rodríguez Roberto, Fragoso-Jarillo Lorena, Garrido-Castro Alberto F, Maestro M Carmen, Fernández-Salas Jose A, Alemán José

机构信息

Organic Chemistry Department, Universidad Autónoma de Madrid Módulo 2 28049 Madrid Spain

Institute for Advanced Research in Chemical Sciences (IAdChem), Universidad Autónoma de Madrid Madrid Spain.

出版信息

Chem Sci. 2022 May 6;13(22):6512-6518. doi: 10.1039/d2sc01799g. eCollection 2022 Jun 7.

DOI:10.1039/d2sc01799g
PMID:35756520
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9172443/
Abstract

Herein, we report, a general, facile and environmentally friendly Minisci-type alkylation of -heteroarenes under simple and straightforward electrochemical conditions using widely available alkyl halides as radical precursors. Primary, secondary and tertiary alkyl radicals have been shown to be efficiently generated and coupled with a large variety of -heteroarenes. The method presents a very high functional group tolerance, including various heterocyclic-based natural products, which highlights the robustness of the methodology. This applicability has been further proved in the synthesis of various interesting biologically valuable building blocks. In addition, we have proposed a mechanism based on different proofs and pieces of electrochemical evidence.

摘要

在此,我们报道了一种通用、简便且环境友好的方法,即在简单直接的电化学条件下,使用广泛可得的卤代烃作为自由基前体,对含氮杂芳烃进行类似Minisci反应的烷基化反应。伯、仲和叔烷基自由基已被证明能有效生成,并与多种含氮杂芳烃发生偶联。该方法对官能团具有很高的耐受性,包括各种基于杂环的天然产物,这突出了该方法的稳健性。这种适用性在各种有趣的具有生物价值的结构单元的合成中得到了进一步证明。此外,我们基于不同的证据和电化学证据提出了一种机理。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7008/9172443/f960352d173e/d2sc01799g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7008/9172443/4d7647578ab8/d2sc01799g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7008/9172443/f960352d173e/d2sc01799g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7008/9172443/4d7647578ab8/d2sc01799g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7008/9172443/f960352d173e/d2sc01799g-s1.jpg

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