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镍催化的二烯和活化烯烃导向的 C6-选择性 2-吡啶酮 C-H 烷基化反应。

Nickel-Catalyzed Directed C6-Selective C-H Alkylation of 2-Pyridones with Dienes and Activated Alkenes.

机构信息

Department of Applied Chemistry, Graduate School of Engineering, Osaka University , Suita, Osaka 565-0871, Japan.

出版信息

J Org Chem. 2017 May 19;82(10):5337-5344. doi: 10.1021/acs.joc.7b00682. Epub 2017 May 8.

Abstract

A pyridine-directed, C6-selective nickel-catalyzed ring-contracting C-H alkylation of 2-pyridones with 1,5-cyclooctadiene (cod) has been developed. The reaction proceeds smoothly under external-ligand-free conditions and is accelerated uniquely by a KPO base. Preliminary mechanistic investigations with deuterium-labeled substrates and related reactions with some alkenes are also disclosed.

摘要

发展了一种吡啶导向的、C6-选择性镍催化的 2-吡啶酮与 1,5-环辛二烯(cod)的环收缩 C-H 烷基化反应。该反应在外加配体自由的条件下顺利进行,并且仅被 KPO 碱加速。还披露了用氘标记的底物进行的初步机理研究和与一些烯烃的相关反应。

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