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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.
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 calculationPublikationsverlauf
Eingereicht: 15. Mai 2022
Angenommen nach Revision: 30. Mai 2022
Accepted Manuscript online:
30. Mai 2022
Artikel online veröffentlicht:
21. Juni 2022
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References
- 1 Tabolin AA, Ioffe SL. Chem. Rev. 2014; 114: 5426
- 2 Bamberger E. Ber. Dtsch. Chem. Ges. 1894; 27: 1548
- 3a Kouznetsov VV, Zubkov FI, Nikitina EV, Duarte LD. A. Tetrahedron Lett. 2004; 45: 1981
- 3b Hojczyk KN, Feng P, Zhan C, Ngai MY. Angew. Chem. Int. Ed. 2014; 53: 14559
- 3c Nakamura I, Jo T, Ishida Y, Tashiro H, Terada M. Org. Lett. 2017; 19: 3059
- 4a Behrman EJ. Beilstein J. Org. Chem. 2006; 2: No. 22
- 4b Wang Y, Liu L, Zhang L. Chem. Sci. 2013; 4: 739
- 4c Wang H.-Y, Anderson LL. Org. Lett. 2013; 15: 3362
- 4d Yuan H, Guo L, Liu F, Miao Z, Feng L, Gao H. ACS Catal. 2019; 9: 3906
- 5 Porzelle A, Woodrow MD, Tomkinson NC. O. Org. Lett. 2010; 12: 1492
- 6 Xiong F, Lu L, Sun T.-Y, Wu Q, Yan D, Chen Y, Zhang X, Wei W, Lu Y, Sun W.-Y, Li JJ, Zhao J. Nat. Commun. 2017; 8: 15912
- 7 Xiong F, Zuo Y, Song Y, Zhang L, Zhang X, Xu S, Ren Y. Org. Lett. 2020; 22: 3799
- 8a Guo L, Liu F, Wang L, Yuan H, Feng L, Kurti L, Gao H. Org. Lett. 2019; 21: 2894
- 8b Guo L, Liu F, Wang L, Yuan H, Feng L, Lu H, Gao H. Org. Chem. Front. 2020; 7: 1077
- 8c Yuan H, Du Y, Liu F, Guo L, Sun Q, Feng L, Gao H. Chem. Commun. 2020; 56: 8226
- 8d Wang M, Liu Y, Wang L, Lu H, Feng L, Gao H. Adv. Synth. Catal. 2021; 363: 1733
- 9a Zhang Z, Luo J, Gao H. Org. Lett. 2021; 23: 9332
- 9b Du Y, Xi Z, Guo L, Lu H, Feng L, Gao H. Tetrahedron Lett. 2021; 72: 153074
- 10 Liu Y, Bai S, Du Y, Qi X, Gao H. Angew. Chem. Int. Ed. 2022; 61: e202115611
- 11 Chatelain P, Sau A, Rowley CN, Moran J. Angew. Chem. Int. Ed. 2019; 58: 14959
- 12 Steensma RW, Galabi S, Tagat JR, McCombie SW. Tetrahedron Lett. 2001; 42: 2281
- 13 Watanabe T, Ueda S, Inuki S, Oishi S, Fujii N, Ohno H. Chem. Commun. 2007; 4516