K2S2O8/H2O/NaOTf System-Promoted Schmidt Rearrangement Reaction of Vinyl Azides

doi:10.6023/cjoc201801025

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (7): 1823-1828.DOI: 10.6023/cjoc201801025 Previous Articles Next Articles

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K₂S₂O₈/H₂O/NaOTf体系促进的烯基叠氮类化合物的Schmidt重排反应

徐峥, 周丙伟, 金红卫, 刘运奎

浙江工业大学化学工程学院绿色化学与技术国家重点实验室培育基地杭州 310014

收稿日期:2018-01-18 修回日期:2018-03-19 发布日期:2018-04-04
通讯作者: 刘运奎 E-mail:ykuiliu@zjut.edu.cn
基金资助:
国家自然科学基金（Nos.21772176，21372201）、浙江工业大学“省重中之重一级学科”开放基金资助项目.

K₂S₂O₈/H₂O/NaOTf System-Promoted Schmidt Rearrangement Reaction of Vinyl Azides

Xu Zheng, Zhou Bingwei, Jin Hongwei, Liu Yunkui

State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Received:2018-01-18 Revised:2018-03-19 Published:2018-04-04
Contact: 10.6023/cjoc201801025 E-mail:ykuiliu@zjut.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21772176, 21372201), the Opening Foundation of Zhejiang Key Course of Chemical Engineering and Technology, Zhejiang University of Technology.

1. K₂S₂O₈/H₂O/NaOTf System-Promoted Schmidt Rearrangement Reaction of Vinyl Azides.PDF(2556KB)

Abstract

Under neutral reaction conditions, sodium triflate promotes the radical reaction of potassium persulfate with water to yield a proton which induces Schmidt rearrangement of alkenyl azides. A variety of substituted acetanilide compounds were synthesized in one step. To obtain the optimal reaction conditions, an arrange of reaction parameters such as radical initiator, solvent, temperature, and reaction time have been screened. This reaction features an easy accessibility of starting materials, simple operation, broad substrate scope and so on. We finally proposed the plausible mechanism based on the mechanistic studies and previous literature.

Key words: vinyl azides, acetanilides, radical reaction, Schmidt rearrangement

Cite this article

Xu Zheng, Zhou Bingwei, Jin Hongwei, Liu Yunkui. K₂S₂O₈/H₂O/NaOTf System-Promoted Schmidt Rearrangement Reaction of Vinyl Azides[J]. Chin. J. Org. Chem., 2018, 38(7): 1823-1828.

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[1] (a) Sana, S.; Rajanna, K. C.; Reddy, K. R.; Bhooshan, M.; Venkateswarlu, M.; Kumar, M. S.; Uppalaiah, K. Green Sustainable Chem. 2012, 2, 97.
(b) Sana, S.; Rajanna, K. C.; Ali, M. M.; Saiprakash, P. K. Chem. Lett. 2000, 48.
[2] Sultane, P. R.; Mete, T. B.; Bhat, R. G. Org. Biomol. Chem. 2014, 12, 261.
[3] Li, Y.; Zhou, Y.-X.; Ma, X.; Jiang, H.-L. Chem. Commun. 2016, 52, 4199.
[4] Wrobleski, A.; Coombs, T. C.; Huh, C. W.; Li, S.-W.; Aubé, J. Org. React. 2012, 78, 1.
[5] (a) Schmidt, K. F. Angew. Chem. 1923, 36, 511.
(b) Schmidt, K. F. Ber. 1924, 57, 704.
[6] Motiwala, H. F.; Fehl, C.; Li, S.-W.; Hirt, E.; Porubsky, P.; Aubé, J. J. Am. Chem. Soc. 2013, 135, 9000.
[7] (a) Insuasty, D.; Robledo, S. M.; Velez, I. D.; Cuervo, P.; Insuasty, B.; Quiroga, J.; Nogueras, M.; Cobo, J.; Abonia, R. Eur. J. Med. Chem. 2017, 141, 567.
(b) Mor, M.; Pahal, P. Pharm. Chem. 2016, 8, 296.
[8] Yu, C.-J.; Li, R.; Gu, P.-M. Tetrahedron Lett. 2016, 57, 3568.
[9] Chen, P.; Sun, C.-H.; Wang, Y.; Xue, Y.; Chen, C.; Shen, M.-H.; Xu, H.-D. Org. Lett. 2018, 20, 1643.
[10] (a) Chan, W.-H.; Somal, G. K.; Katz, C. E.; Pei, H.-X.; Zeng, Y.-B.; Douglas, J. T.; Aube, J. J. Org. Chem. 2009, 74, 7618.
(b) Meyer, A. M.; Katz, C. E.; Li, S.-W.; Velde, D. V.; Aube, J. Org. Lett. 2010, 12, 1244.
[11] Song, X.-R.; Qiu, Y.-F.; Song, B.; Hao, X.-H.; Han, Y.-P.; Gao, P.; Liu, X.-Y.; Liang, Y.-M. J. Org. Chem. 2015, 80, 2263.
[12] Kim, C.; Kang, S.; Rhee, Y.-H. J. Org. Chem. 2014, 79, 11119.
[13] (a) Wang, Y.-F.; Lonca, G. H.; Runigo, M.; Chiba, S. Org. Lett. 2014, 16, 4272.
(b) Mackay, E. G.; Studer, A. Chem.-Eur. J. 2016, 22, 1.
(c) Sun, X.-Y.; Yu, S.-Y. Chem. Commun. 2016, 52, 10898.
(d) Yang, J.-C.; Zhang, J.-J.; Guo, L.-N. Org. Biomol. Chem. 2016, 14, 9806.
[14] (a) Hassner, A.; Ferdinandi, E. S.; Isbister, R. J. J. Am. Chem. Soc. 1970, 92, 1672.
(b) Zhang, F.-L.; Wang, Y.-F.; Lonca, G.-H.; Zhu, X.; Chiba, S. Angew. Chem., Int. Ed. 2014, 53, 4390.
(c) Zhang, F.-L.; Zhu, X.; Chiba, S. Org. Lett. 2015, 17, 3138.
[15] (a) Lu, S.-C.; Gong, Y.-L.; Zhou, D.-M. J. Org. Chem. 2015, 80, 9336.
(b) Kianmehr, E.; Faghih, N.; Karaji, S.; Lomedasht, Y. A.; Khan, K. M. J. Organomet. Chem. 2016, 801, 10.
(c) Yadav, A. K.; Yadav, L. S. Tetrahedron Lett. 2016, 57, 1489.
[16] Zhang, J.; Chen, M.-Y.; Zhu, L. RSC Adv. 2016, 6, 758.
[17] Gaydou, M.; Echavarren, A. M. Angew. Chem., Int. Ed. 2013, 52, 13468, and references cited therein.
[18] Wang, Y.-F.; Toh, K. K.; Lee, J.-Y.; Chiba, S. Angew. Chem., Int. Ed. 2011, 50, 5927, and references cited therein.
[19] (a) Jones, B. Chem. Rev. 1944, 35, 335.
(b) Sun, C.; Zhang, B.; Huang, X.; Yu, J. Chin. J. Org. Chem. 2018, 457 (in Chinese).
(孙超, 姚武冰, 张斌. 黄相韵, 虞姜姜, 有机化学, 2018, 38, 457.)
[20] Yang, S.-D.; Li, B.-J.; Wan, X.-B.; Shi, Z.-J. J. Am. Chem. Soc. 2007, 129, 6066.
[21] Ernest, W.; Barnett, B. F. J. Am. Chem. Soc. 1960, 82, 4671.
[22] Peter, T. W. C.; Zheng, N.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 14560.
[23] H Xi, J.; Dong, Q.-L.; Liu, G.-S.; Wang, S.-Z.; Chen, L.; Yao, Z.-J. Synlett 2010, 1674.
[24] Fuson, R. C.; Talbom, R. L. J. Org. Chem. 1961, 26, 2674.
[25] Antonchick, A. P.; Samanta, R.; Kulikov, K.; Lategahn, J. Angew. Chem., Int. Ed. 2011, 50, 8605.
[26] Tsukamoto, H.; Suzuki, R.; Kondo, Y. J. Comb. Chem. 2006, 8, 289.
[27] Cho, G.-Y.; Remy, P.; Jansson, J.; Moessner, C.; Bolm, C. Org. Lett. 2004, 6, 3293.
[28] Fors, B. P.; Dooleweerdt, K.; Zeng, Q.-L.; Buchwald, S. L. Tetrahedron 2009, 65, 6576.
[29] Bedford, R. B.; Haddow, M. F.; Mitchell, C. J.; Webster, R. L. Angew. Chem., Int. Ed. 2011, 50, 5524.
[30] Chen, C.-T.; Kuo, J.-H.; Pawar, V. D.; Munot, Y. S.; Weng, S.-S.; Ku, C.-H.; Liu, C.-Y. J. Org. Chem. 2005, 70, 1188.
[31] Epishina, M. A.; Kuliov, A. S.; Ignatev, N. V.; Schuite, M.; Makhova, N. N. Mendeleev Commun. 2010, 20, 335.
[32] Taylor, E. J.; Jones, M. D.; Williams, J. M. J.; Bull, S. D. J. Org. Chem. 2012, 77, 2808.
[33] Huang X.-H.; Anderson, K. W.; Zim D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
[34] Kajihara, K.; Arisawa, M.; Shuto, S. J. Org. Chem. 2008, 73, 9494.
[35] Cam-Van, N. T.; Diep, B. K.; Buu-Hoi, N. P. Tetrahedron 1964, 20, 2195.
[36] Antonow, D.; Marrafa, T.; Dawood, I.; Ahmed, T.; Haque, M. R.; Thurston, D. E.; Zinzalla, G. Chem. Commun. 2010, 46, 2289.
[37] Sykulski, J. Acta Pol. Pharm. 1963, 20, 131.
[38] Liu, H.; Wang, X.-M.; Gu, Y.-H.; Org. Biomol. Chem. 2011, 9, 1614.

K₂S₂O₈/H₂O/NaOTf体系促进的烯基叠氮类化合物的Schmidt重排反应

K₂S₂O₈/H₂O/NaOTf System-Promoted Schmidt Rearrangement Reaction of Vinyl Azides

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K2S2O8/H2O/NaOTf体系促进的烯基叠氮类化合物的Schmidt重排反应