Issue 97, 2023
From the journal:

Chemical Communications

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

Xiaofei Zhang, ORCID logo *a   Yao Wang,a   Jiaxin Liu,a   Chengpeng Tian,a   Xiang Li, ORCID logo a   Pan Xie, ORCID logo a   Zhenyu Zhu ORCID logo *a  and  Tuanli Yao ORCID logo *a  

* 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.

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

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

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

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

Permissions

Request permissions

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements