Issue 5, 2022

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
08 okt 2021
Accepted
05 yan 2022
First published
06 yan 2022

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

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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