[2,3]-Sigmatropic Rearrangement of Arylhydroxylamines: Rapid Access to ortho-Sulfonylated Anilines

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 calculation

Publication 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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