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

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Article information

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

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

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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

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