From Hydroxylamines to Anilines via Trifluoroacetic Anhydride (TFAA) Assisted Stieglitz Rearrangement
- Corresponding author: Jiao Ning, jiaoning@pku.edu.cn
Citation: Luo Xiao, Jiao Ning. From Hydroxylamines to Anilines via Trifluoroacetic Anhydride (TFAA) Assisted Stieglitz Rearrangement[J]. Acta Chimica Sinica, ;2020, 78(8): 758-762. doi: 10.6023/A20050191
(a) Piechnick, R.; Heck, M.; Sommer, M. E. Biochemistry 2011, 50, 7168; (b) Chen, Y.; Wang, X.; Xiang, W.; He, L.; Tang, M.; Wang, F.; Wang, T.; Yang, Z.; Yi, Y.; Wang, H.; Niu, T.; Zheng, L.; Lei, L.; Li, X.; Song, H.; Chen, L. J. Med. Chem. 2016, 59, 5488.
For some examples in recent years: (a) Nguyen, T. B.; Martel, A.; Dhal, R.; Dujardin, G. Org. Lett. 2008, 10, 4493; (b) Guimond, N.; MacDonald, M. J.; Lemieux, V.; Beauchemin, A. M. J. Am. Chem. Soc. 2012, 134, 16571; (c) Pusterla, I.; Bode, J. W. Angew. Chem. Int. Ed. 2012, 51, 513; (d) Li, J.; He, Y.; Ren, X.; Shi, X.; Yang, S.; Gao, X.; Huang, G. Chin. J. Chem. 2013, 31, 1003; (e) Hesp, C. R.; MacDonald, M. J.; Zahedi, M. M.; Bilodeau, D. A.; Zhao, S. B.; Pesant, M.; Beauchemin, A. M. Org. Lett. 2015, 17, 5136; (f) Sun, H. B.; Gong, L.; Tian, Y. B.; Wu, J. G.; Zhang, X.; Liu, J.; Fu, Z.; Niu, D. Angew. Chem. Int. Ed. 2018, 57, 9456.
(a) Stieglitz, J.; Leech, P. N. Ber. 1913, 46, 2147; (b) Stieglitz, J.; Leech, P. N. J. Am. Chem. Soc. 1914, 36, 272. (c) Morgan, A. F. J. Am. Chem. Soc. 1916, 38, 2095; (d) Newman, M. S.; Hay, P. M. J. Am. Chem. Soc. 1953, 75, 2322; (e) Stolyarov, B. V.; Krylov, A. I.; Ioffe, B. V. Zh. Org. Khim. 1977, 13, 2004.
Colomer, I.; Chamberlain, A. E. R.; Haughey, M. B.; Donohoe, T. J. Nat. Rev. Chem. 2017, 1, 0088.
doi: 10.1038/s41570-017-0088
(a) Mlynarski, S. N.; Karns, A. S.; Morken, J. P. J. Am. Chem. Soc. 2012, 134, 16449; (b) Xiao, Q.; Tian, L.; Tan, R.; Xia, Y.; Qiu, D.; Zhang, Y.; Wang, J. Org. Lett. 2012, 14, 4230; (c) Zhu, C.; Li, G.; Ess, D. H.; Falck, J. R.; Kurti, L. J. Am. Chem. Soc. 2012, 134, 18253; (d) Voth, S.; Hollett, J. W.; McCubbin, J. A. J. Org. Chem. 2015, 80, 2545.
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