Issue 19, 2020
From the journal:

Organic & Biomolecular Chemistry

Study on the ArI-catalyzed intramolecular oxy-cyclization of 2-alkenylbenzamides to benzoiminolactones†

Huixia Liu,a   Xiaojun Deng,a   Xie Huang,a   Nan Jia  and  Wei He ORCID logo *a  

* Corresponding authors

a Department of Chemistry, School of Pharmacy, The Fourth Military Medical University, 169 Changle West Road, Xi'an 710032, P. R. China
E-mail: weihechem@fmmu.edu.cn

Abstract

A new intramolecular oxy-cyclization of 2-alkenylbenzamides catalyzed by ArI has been developed. This protocol is highlighted by its metal-free catalytic system and extremely short reaction time, providing efficient and straightforward access to various benzoiminolactones in good to excellent yields. Interestingly, a regioselective transformation occurred when using two different reaction systems. Mechanistic studies suggested that mCPBA acts as both oxidant and ligand at the IIII center, and the Lewis acid BF3 accelerated ligand exchange and reductive elimination in the catalytic process.

Graphical abstract: Study on the ArI-catalyzed intramolecular oxy-cyclization of 2-alkenylbenzamides to benzoiminolactones

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Article information

DOI
https://doi.org/10.1039/D0OB00612B
Article type
Communication
Submitted
24 Mar 2020
Accepted
21 Apr 2020
First published
23 Apr 2020

Org. Biomol. Chem., 2020,18, 3654-3658

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Study on the ArI-catalyzed intramolecular oxy-cyclization of 2-alkenylbenzamides to benzoiminolactones

H. Liu, X. Deng, X. Huang, N. Ji and W. He, Org. Biomol. Chem., 2020, 18, 3654 DOI: 10.1039/D0OB00612B

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