芳基烯烃的电化学硝基酰化双官能化反应。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-06-25 DOI:10.1021/acs.joc.5c00510

Feng Zhang, Xiangxi Liu, Yi Yin, Weixing Chang, Lingyan Liu* and Jing Li*,

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引用次数: 0

摘要

提出了一种新的烯烃硝基酰化双官能化电化学反应。以亚硝酸钠为硝基自由基前体，在一锅中同时形成C-C键和C-N键是史无前例的，得到了一系列收率较高的α-芳基-β-硝基衍生物。此外，还通过SN2途径中的溴化中间体提出了烯烃双官能化反应的合理机制。此外，该方法还制备了一种昂贵的大麻素CB1受体正变构调节剂ZCZ011。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Electrochemical Nitroindolylation Bifunctionalization Reaction of Arylalkenes

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Electrochemical Nitroindolylation Bifunctionalization Reaction of Arylalkenes

A novel electrochemical nitroindolylation bifunctionalization reaction of alkenes was developed. It was unprecedented that both C–C and C–N bonds were concurrently formed using sodium nitrite as the nitro free radical precursor in one pot. A series of α-aryl-β-nitroindole derivatives was generated in good to high yields. Moreover, a plausible mechanism for this bifunctionalization reaction of alkenes was proposed via a bromonitro intermediate in an S_N2 pathway. In addition, ZCZ011, an expensive positive allosteric modulator of the cannabinoid CB1 receptor, was facilely synthesized using this method.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.