I2-catalyzed synthesis of 3-aminopyrrole with homopropargylic amines and nitrosoarenes

Jiaze Qin; Shixuan Jiang; Xiaofeng Luo; Tianqiang Wang; Peihua Liu; Bingxiang Yuan; Rulong Yan

doi:10.1039/D4CC00482E

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I₂-catalyzed synthesis of 3-aminopyrrole with homopropargylic amines and nitrosoarenes†

Jiaze Qin,‡^a Shixuan Jiang,‡^a Xiaofeng Luo,^b Tianqiang Wang,^b Peihua Liu,^c Bingxiang Yuan^a and Rulong Yan

*^a

Author affiliations

* Corresponding authors

^a State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 73000, Gansu, China
E-mail: yanrl@lzu.edu.cn
Fax: +86 0931-8912596

^b Chengdu Guibao Science and Technology Co., Ltd, Chengdu 610041, Sichuan, China

^c Research Institute of Oil and Gas Technology of Changqing Oilfield Company, Xian 710018, Shaanxi, China

Abstract

The synthesis of 3-aminopyrrole using the amination reagent nitrosoarenes and homopropargylic amines catalyzed by I₂ through cyclization and amination has been developed. This protocol features excellent functional group tolerance and mild reaction conditions, yielding 3-aminopyrroles in moderate to good yields without a metal catalyst. This method realizes the construction and amination of the 3-aminopyrroles in which nitrosoarenes serve as the amine source and oxidant.

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Article information

DOI: https://doi.org/10.1039/D4CC00482E
Article type: Communication
Submitted: 31 Jan 2024
Accepted: 06 Mar 2024
First published: 06 Mar 2024

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Chem. Commun., 2024,60, 3701-3704

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I₂-catalyzed synthesis of 3-aminopyrrole with homopropargylic amines and nitrosoarenes

J. Qin, S. Jiang, X. Luo, T. Wang, P. Liu, B. Yuan and R. Yan, Chem. Commun., 2024, 60, 3701 DOI: 10.1039/D4CC00482E

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