Synthesis of 3-aminotetrahydro-1H-carbazols by visible-light photocatalyzed cycloaddition of cyclopropylanilines with 2-alkenylarylisocyanides

Xiaofei Zhang; Yao Wang; Jiaxin Liu; Chengpeng Tian; Xiang Li; Pan Xie; Zhenyu Zhu; Tuanli Yao

doi:10.1039/D3CC04674E

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Synthesis of 3-aminotetrahydro-1H-carbazols by visible-light photocatalyzed cycloaddition of cyclopropylanilines with 2-alkenylarylisocyanides†

Xiaofei Zhang,

*^a Yao Wang,^a Jiaxin Liu,^a Chengpeng Tian,^a Xiang Li,

^a Pan Xie,

^a Zhenyu Zhu

*^a and Tuanli Yao

*^a

Author affiliations

* Corresponding authors

^a Key Laboratory of Chemical Additives for China National Light Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi’an, China
E-mail: yaotuanli@sust.edu.cn

Abstract

A visible-light-induced cycloaddition between 2-alkenylarylisocyanides and cyclopropylanilines is reported. This cascade radical reaction constructs two new C–C bonds and two rings to afford 3-aminotetrahydro-1H-carbazols with high atom and step economy. The mechanism is rationalized as involving sequential distonic radical cation formation/isocyanide insertion/5-exo-trig cyclization/intramolecular iminium ion addition/tautomerization.

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DOI: https://doi.org/10.1039/D3CC04674E
Article type: Communication
Submitted: 20 Sep 2023
Accepted: 12 Nov 2023
First published: 13 Nov 2023

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Chem. Commun., 2023,59, 14423-14426

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Synthesis of 3-aminotetrahydro-1H-carbazols by visible-light photocatalyzed cycloaddition of cyclopropylanilines with 2-alkenylarylisocyanides

X. Zhang, Y. Wang, J. Liu, C. Tian, X. Li, P. Xie, Z. Zhu and T. Yao, Chem. Commun., 2023, 59, 14423 DOI: 10.1039/D3CC04674E

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Chemical Communications

Synthesis of 3-aminotetrahydro-1H-carbazols by visible-light photocatalyzed cycloaddition of cyclopropylanilines with 2-alkenylarylisocyanides†

Abstract

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Synthesis of 3-aminotetrahydro-1H-carbazols by visible-light photocatalyzed cycloaddition of cyclopropylanilines with 2-alkenylarylisocyanides

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