Issue 5, 2022
From the journal:

Organic Chemistry Frontiers

S-triggered Schmidt-type rearrangement of vinyl azides to access N-aryl-(trifluoromethylsulfinyl)acetamides†

Zhenhua Liu,a   Tian Yu,a   Longhua Li,a   Wei Fu,b   Xingxing Gan,a   Huimin Chen,a   Wen Gao*a  and  Bo Tang ORCID logo *a  

* Corresponding authors

a College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Institute of Biomedical Sciences, Shandong Normal University, Jinan 250014, P.R. China
E-mail: gaowen@sdnu.edu.cn, tangb@sdnu.edu.cn

b Department of Pharmacy, Zibo Central Hospital, Zibo 255000, P. R. China

Abstract

A novel S-induced Schmidt-type rearrangement of vinyl azides with CF3SO2Na is reported, which is mediated by triphosgene (BTC) under mild reaction conditions. A wide range of N-arylated 2-(trifluoromethylsulfinyl)acetamides, for the first time, were successfully obtained in good yields, through sequential trifluoromethylsulfinylation and aryl 1,2-migration.

Graphical abstract: S-triggered Schmidt-type rearrangement of vinyl azides to access N-aryl-(trifluoromethylsulfinyl)acetamides

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/D1QO01516H
Article type
Research Article
Submitted
08 ኦክቶ 2021
Accepted
05 ጃንዩ 2022
First published
06 ጃንዩ 2022

Org. Chem. Front., 2022,9, 1241-1246

Permissions

Request permissions

S-triggered Schmidt-type rearrangement of vinyl azides to access N-aryl-(trifluoromethylsulfinyl)acetamides

Z. Liu, T. Yu, L. Li, W. Fu, X. Gan, H. Chen, W. Gao and B. Tang, Org. Chem. Front., 2022, 9, 1241 DOI: 10.1039/D1QO01516H

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