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切换镍催化的2-吡啶酮与炔烃反应的反应活性:简便合成多芳基/多烷基喹啉酮

Switching the Reactivity of the Nickel-Catalyzed Reaction of 2-Pyridones with Alkynes: Easy Access to Polyaryl/Polyalkyl Quinolinones.

作者信息

Prusty Namrata, Mohanty Smruti Ranjan, Banjare Shyam Kumar, Nanda Tanmayee, Ravikumar Ponneri C

机构信息

School of Chemical Sciences, National Institute of Science Education and Research (NISER), Bhubaneswar, 752050 Odisha, India.

Homi Bhabha National Institute, Training School Complex, Anushaktinagar, Mumbai 400094, India.

出版信息

Org Lett. 2022 Aug 26;24(33):6122-6127. doi: 10.1021/acs.orglett.2c02021. Epub 2022 Aug 11.

DOI:10.1021/acs.orglett.2c02021
PMID:35952663
Abstract

A Ni-catalyzed C6 followed by C5 cascade C-H activation/[2 + 2 + 2] annulation of 2-pyridone with alkynes has been achieved. A change in the reaction pathway was achieved by tuning the reaction conditions and incorporating a directing group. A wide variety of substrates and alkynes are amenable to this transformation. The key to success for this transformation is the use of sodium iodide as an additive. More importantly, we detected the five-membered metallacycle intermediate through HRMS wherein iodide is ligated to the metal.

摘要

实现了镍催化的2-吡啶酮与炔烃的C6接着C5级联C-H活化/[2 + 2 + 2]环化反应。通过调整反应条件和引入导向基团实现了反应途径的改变。多种底物和炔烃都适用于这种转化。这种转化成功的关键是使用碘化钠作为添加剂。更重要的是,我们通过高分辨质谱检测到了五元金属环中间体,其中碘化物与金属相连。

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