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镍催化的炔基芳基碘的电化学环化反应及与醛的多米诺反应

Nickel-Catalyzed Electrochemical Cyclization of Alkynyl Aryl Iodide and the Domino Reaction with Aldehydes.

作者信息

Déjardin Claire, Renou Amaury, Maddaluno Jacques, Durandetti Muriel

机构信息

Normandie Univ, UNIROUEN, INSA Rouen, CNRS, Laboratoire COBRA (UMR 6014 & FR 3038), 76000 Rouen, France.

出版信息

J Org Chem. 2021 Jul 2;86(13):8882-8890. doi: 10.1021/acs.joc.1c00811. Epub 2021 Jun 11.

DOI:10.1021/acs.joc.1c00811
PMID:34115504
Abstract

An intramolecular carbometallation of a triple bond promoted by electrochemistry and mediated by nickel catalysis is described. This domino process transforms various aryl halides bearing a propargyl chain into substituted heterocycles in one single operation, with high stereoselectivities and in good to high yields. This reaction, characterized by a cyclic voltammetry set of experiments, proceeds following a -- cyclization process. When run at 80 °C, vinylbenzofuranes that are suitable substrates for cycloaddition reactions are obtained.

摘要

描述了一种由电化学促进并由镍催化介导的三键分子内碳金属化反应。这种多米诺过程能在一次操作中将各种带有炔丙基链的芳基卤化物转化为取代杂环，具有高立体选择性且产率良好至高。该反应通过一组循环伏安实验表征，遵循一个环化过程进行。在80℃下进行反应时，可得到适用于环加成反应的乙烯基苯并呋喃。

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