Copper-Catalyzed Hydroamination of 2-Alkynylazobenzenes: Synthesis of 3-Alkenyl-2H-Indazoles

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

The Journal of Organic Chemistry Pub Date : 2024-11-02 DOI:10.1021/acs.joc.4c0214410.1021/acs.joc.4c02144

Clara Mañas, Juan Herrero-Bourdieu and Estíbaliz Merino*,

引用次数: 0

Abstract

A copper-catalyzed intramolecular synthesis of 3-alkenyl-2H-indazoles from 2-alkynylazobenzenes is described. The reaction proceeds in a single step via C–N bond formation and a subsequent 1,2-hydride shift, affording products in high yields. DFT calculations suggest the 1,2-hydride shift as the rate-determining step. Further derivatization enables functionalization of the 3-alkenyl-2H-indazoles.

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铜催化的 2-炔基偶氮苯氢化反应：合成 3-烯基-2H-吲唑

本文介绍了一种铜催化的分子内合成法，从 2-炔基偶氮苯合成 3-烯基-2H-吲唑。该反应通过 C-N 键的形成和随后的 1,2-酸酐转移在一个步骤中进行，并以高产率得到产物。DFT 计算表明，1,2-酸酐转移是决定反应速率的步骤。进一步衍生可使 3-烯基-2H-吲唑官能化。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

The 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： The 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.