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DOI: 10.1055/a-1863-9090
[2,3]-Sigmatropic Rearrangement of Arylhydroxylamines: Rapid Access to ortho-Sulfonylated Anilines
We gratefully acknowledge the National Natural Science Foundation of China (21702122) and the Key Technology Research and Development Program of Shandong Province (2019GSF108056) for financial support.
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Abstract
In the absence of transition-metal catalysts and additional oxidants, arylhydroxylamines can undergo an unconventional O-sulfinylation/[2,3]-sigmatropic rearrangement/rearomatization cascade with trifluoromethylsulfinyl chloride to rapidly and efficiently synthesize versatile ortho-sulfonylated aromatic amines. This Synpacts article describes the discovery, further study, and practical application of the rearrangement reactions in arylhydroxylamine compounds and highlights our recent advances in this area.
1 Introduction
2 Discovery of a New Reaction
3 O-Sulfinylation of Arylhydroxylamines Followed by [2,3]-σ Rearrangement
4 Conclusion
Key words
arylhydroxylamines - ortho-sulfonylated anilines - sigmatropic rearrangement - trifluoromethanesulfonylation - DFT calculationPublication History
Received: 15 May 2022
Accepted after revision: 30 May 2022
Accepted Manuscript online:
30 May 2022
Article published online:
21 June 2022
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