Synthesis of Alkyl Sulfate from α-Trifluoromethylbenzylbromide—An Extension of Sulfinatodehalogenation

doi:10.6023/cjoc201810022

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 144-150.DOI: 10.6023/cjoc201810022 Previous Articles Next Articles

Special Issue: 庆祝陈庆云院士九十华诞

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从α-三氟甲基苄溴合成烷基硫酸盐——脱卤亚磺化反应的延伸

付晓林^a, 孙岩^b, 赵志刚^a, 郭勇^b, 陈庆云^b, 念保义^c

a 西南民族大学化学与环境保护工程学院成都 610041;
b 中国科学院上海有机化学研究所上海 200032;
c 三明学院三明氟化工产业技术研究院三明 365004

收稿日期:2018-10-18 修回日期:2018-11-24 发布日期:2018-11-30
通讯作者: 孙岩, 赵志刚 E-mail:sunyan@sioc.ac.cn;zzg63129@163.com
基金资助:
国家自然科学基金（Nos.21737004，21672239，21421002）和三明市氟化工产业技术研究院（Nos.FCIT201704GR，FCIT201705GR，FCIT201701BR）资助项目.

Synthesis of Alkyl Sulfate from α-Trifluoromethylbenzylbromide—An Extension of Sulfinatodehalogenation

Fu Xiaolin^a, Sun Yan^b, Zhao Zhigang^a, Guo Yong^b, Chen Qingyun^b, Nian Baoyi^c

a College of Chemistry & Environment Protection Engineering, Southwest Minzu University, Chengdu 610041;
b College of Chemistry & Environment Protection Engineering, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
c Sanming Institute of Fluorochemical Industry, Sanming University, Sanming 365004

Received:2018-10-18 Revised:2018-11-24 Published:2018-11-30
Contact: 10.6023/cjoc201810022 E-mail:sunyan@sioc.ac.cn;zzg63129@163.com
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21737004, 21672239, 21421002) and the Sanming Institute of Fluorochemical Industry (Nos. FCIT201704GR, FCIT201705GR, FCIT201701BR).

The sulfinatodehalogenation reaction is a common method of introducing a fluoroalkyl group. In this paper, the reaction of α-trifluoromethylbenzyl bromide under sulfinatodehalogenation conditions was investigated. It was found that the product was an sodium alkyl sulfate (ArCH(CF₃)OSO₃Na) instead of an sodium alkyl sulfinate (ArCH(CF₃)SO₂Na) which was normal produced. α-Trifluoromethylbenzyl bromide did not react with the olefin after its generation of a radical intermediate under sulfinatodehalogenation conditions even though an olefin was presented. Instead, the reaction directly gave an alkyl sulfinate, and then oxidized by air to provide a product as an alkyl sulfate.

Key words: Trifiluoromethyl, free radical, sulfinatodehalogenation, alkyl sulfate

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Fu Xiaolin, Sun Yan, Zhao Zhigang, Guo Yong, Chen Qingyun, Nian Baoyi. Synthesis of Alkyl Sulfate from α-Trifluoromethylbenzylbromide—An Extension of Sulfinatodehalogenation[J]. Chin. J. Org. Chem., 2019, 39(1): 144-150.

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[1] (a) Huang, W.-Y. Organofluorine Chemistry in China, Shanghai Scientific and Technical Publishers, Shanghai, 1996 (in Chinese). (黄维垣, 中国有机氟化学研究, 上海科学技术出版社, 上海, 1996.)
(b) Zhang, C.-P.; Guo, Y.; Xiao, J.-C.; Gu, Y.-C. Chem. Soc. Rev. 2012, 41, 4536.
(c) Huang, B.-N.; Huang, W.-Y.; Hu, C.-M. Acta Chim. Sinica 1981, 39, 481(in Chinese). (黄炳南, 黄维垣, 胡昌明, 化学学报, 1981, 39, 481.)
(d) Huang, W.-Y.; Huang, B.-N.; Hu, C.-M. J. Fluorine Chem. 1983, 23, 193(in Chinese).
[2] (a) Qing, F.-L.; Qiu, X.-L. Organofluorine Chemistry, Science Press, Beijing, 2007(in Chinese). (卿凤翎, 邱小龙, 有机氟化学, 科学出版社, 北京, 2007.)
(b) Prakash, K. Modern Fluoroorganic Chemistry. Synthesis, Reactivity, Applications, 2nd ed., Wiley-VCH, Weinheim, 2013.
(c) Uneyama, K. Organofluorine Chemistry, Blackwell, Oxford, UK, 2006.
(d) Valentine, G. N.; Vasiliy, M. M.; Aleksey, V. S. Chem. Rev. 2015, 115, 973.
(e) Zhang, C.-P.; Chen, Q.-Y.; Guo, Y.; Xiao, J.-C.; Gu, Y.-C. Coord. Chem. Rev. 2014, 261, 28.
(f) Guo, Y.; Huang, M.-W.; Fu, X.-L.; Liu, C.; Chen, Q.-Y.; Zhao, Z.-G. Chin. Chem. Lett. 2017, 28, 719.
(g) Li, G.-M.; Sun, D.-Q. Chin. J. Org. Chem. 2016, 36, 1715(in Chinese). (李恭铭, 孙德群, 有机化学, 2016, 36, 1715.)
(h) He, J.-Q.; Lou, S.-J.; Xu, D.-Q. Acta Chim. Sinica 2016, 36, 1218(in Chinese). (何将旗, 娄绍杰, 许丹倩, 化学学报, 2016, 36, 1218.)
(i) Xu, Y.-Y.; Qian, A.-R.; Cao, X.-F.; Ling, C.-Y.; Cao, Y.-B.; Wang, R.-L.; Li, Y.-S.; Yang, Y.-S. Chin. Chem. Lett. 2016, 27, 703.
(j) Fu, L.-N.; Leng, B.; Li, Y.-S.; Gao, X.-K. Chin. Chem. Lett. 2016, 27, 1319.
[3] (a) Han, E.; Guo, Y.; Chen, Q.-Y.; Chin. J. Org. Chem. 2017, 37, 1714(in Chinese). (韩恩健, 郭勇, 陈庆云, 有机化学, 2017, 37, 1714.)
(b) Yang, B.; Xu, X.-H.; Qing, F.-L. Chin. J. Chem. 2016, 34, 465.
(c) Zhang, Z.; Yu, W.; Zhou, Q.; Li, T.; Zhang, Y.; Wang, J. Chin. J. Chem. 2016, 34, 473.
(d) Zhang, B.; Zhang, X.-G. Chin. J. Chem. 2016, 34, 477.
(e) Geng, Q.; Xiao, X.; He, G.-R.; Yao, S.-M.; Liang, G.-X. Chin. Chem. Lett. 2016, 27, 1009.
(f) Zhang, B.-H.; Kong, J.-J.; Huang, Y.; Lou, Y.-G.; Li, X.-F.; He, C.-Y. Chin. Chem. Lett. 2017, 28, 1751.
(g) Liu, Y.-L.; Yin, X.-P.; Zhou, J. Chin. J. Chem. 2018, 36, 321.
[4] (a) Miyake, Y.; Ota, S.-I.; Shibata, M.; Nakajima, K.; Nishibayashi, Y. Org. Biomol. Chem. 2014, 12, 5594.
(b) Egami, H.; Ide, T.; Kawato, Y.; Hamashima, Y. Chem. Commun. 2015, 51, 16675.
(c) Zhu, L.; Liu, S.; Douglas, J. T.; Altman, R. A. Chem. Eur. J. 2013, 19, 12800.
(d) Kuninobu, Y.; Nagase, M.; Kanai, M. Angew. Chem., Int. Ed. 2015, 54, 10263.
(e) Wang, X.; Song, S.; Jiao, N. Chin. J. Chem. 2018, 36, 213~216.
[5] (a) Vukovic, V. D.; Richmond, E.; Wolf, E.; Moran, J. Angew. Chem., Int. Ed. 2017, 56, 3085.
(b) Prakash, G. K. S.; Paknia, F.; Thomas M.; Mathew, T.; Mlostoń, G.; Olah, G. A. Org. Lett. 2011, 13, 4128.
[6] (a) Liang, Y.; Fu, G. C. J. Am. Chem. Soc. 2015, 137, 9523.
(b) Liang, Y.; Fu, G. C. Angew. Chem., Int. Ed. 2015, 54, 9047.
(c) Ryu, D.; Primer, D. N.; Tellis, J. C.; Molander, G. A. Chem. Eur. J. 2016, 22, 120.
(d) Li, X.; Feng, Z.; Jiang, Z.-X.; Zhang, X. Org. Lett. 2015, 17, 5570.
[7] (a) Gao, B.; Zhao, Y.; Hu, J. Angew. Chem., Int. Ed. 2015, 54, 638.
(b) Tang, H.-J.; Zhang, Y.-F.; Jiang, Y.-W.; Feng, C. Org. Lett. 2018, 20, 5190.
(c) Tian, P.; Wang, C.-Q.; Cai, S.-H.; Song, S.; Ye, L.; Feng, C.; Loh, T.-P. J. Am. Chem. Soc. 2016, 138, 15869.
(d) Tang, H.-J.; Lin, L.-Z.; Feng, C.; Loh T.-P. Angew. Chem., Int. Ed. 2017, 56, 9872.
[8] (a) Long, Z.-Y., Chen, Q.-Y. Tetrahedron Lett. 1998, 39, 8487.
(b) Long, Z.-Y.; Chen, Q.-Y. J. Org. Chem. 1999, 64, 4775.
[9] (a) Li, L.; Huang, M.; Liu, C.; Xiao, J.-C.; Chen, Q.-Y.; Guo, Y.; Zhao, Z.-G. Org. Lett. 2015, 17, 4714.
(b) Huang M.; Li, L.; Zhao, Z.-G.; Chen, Q.-Y.; Guo, Y. Synth. Catal. 2015, 47, 3891.
(c) Kreis, L. M.; Krautwald, S.; Pfeiffer, N.; Martin, R. E.; Carreira, E. M. Org. Lett. 2013, 15, 1634.
(d) Rong, J.; Ni, C.; Wang, Y.; Kuang, C.; Gu, Y.; Hu, J. Acta Chim. Sinica 2017, 75, 105.
[10] Huan, F., Chen, Q.-Y., Guo, Y. J. Org. Chem. 2016, 81, 7051.
[11] (a) Kudova, E.; Chodounska, H.; Slavikova, B.; Budesinsky, M.; Nekardova, M.; Vyklicky, V.; Krausova, B.; Svehla, P.; Vyklicky, L. J. Med. Chem. 2015, 58, 5950.
(b) Burlingham, B. T.; Pratt L. M.; Davidson, E. R.; Shiner, V. J.; Jr.; Fong, J.; Widlanski, T. S. J. Am. Chem. Soc. 2003, 125, 13036.
[12] Kamiyama, H.; Kubo, Y.; Sato, H.; Yamamoto, N.; Fukuda, T.; Ishibashi, F.; Iwao, M. Bioorg. Med. Chem. 2011, 19, 7541.
[13] (a) Stastnaa, E.; Chodounskaa, H.; Pouzara, V.; Kaprasa, V.; Borovskaa, J.; Caisc, O.; Jr, L. V. Steroids 2009, 74, 256.
(b) Nishimura, Y.; Shudo, H.; Seto, H.; Hoshino, Y.; Miura, Y. Bioorg. Med. Chem. Lett. 2013, 23, 6390.
[14] (a) Nie, L.; S. Yao; Dong, B.; Li, X.-l.; Song, H. J. Mol. Liq. 2017, 240, 152.
(b) Desoky, A. Y.; Hendel, J.; Ingram L.; Taylor, S. D. Tetrahedron 2011, 67, 1281.
(c) Beichel, W.; Panzer, J. M. U.; Hätty, J. Ye, X.; Himmel, D.; Krossing, I. Angew. Chem., Int. Ed. 2014, 53, 6637.
[15] Dolbier, W. R.; Jr. Guide to Fluorine NMR for Organic Chemists, John Wiley & Sons, Inc., New Jersey, 2009, p. 143.
[16] (a) Brunelle, J. A.; Letendre, L. J.; Weltin, E. E.; Brown, J. H.; Bushweller, C. H. J. Phys. Chem. 1992, 96, 9225.
(b) Tordeux, M.; Wakselman, C.; Jarjayes, O.; Béguin, C. G. Magn. Reson. Chem. 2001, 39, 301.
[17] Wang, R.; Jiang, L.; Yi, W. J. Org. Chem. 2018, 83, 7789.
[18] Dneprovskii, A. S.; Eliseenkov, E. V.; Mil'tsov, S. A. J. Org. Chem. 1982, 2, 365.
[19] Yusuke, Y.; Shoji, H.; Hisanori, S. Tetrahedron 2010, 2, 473.
[20] Okano, T; Fumoto, M; Kusukawa, T; Fujita, M. J. Fluorine Chem. 2002, 9, 91.
[21] Andreea, A. O.; Daweon, R.; Ioana, A.; Gary A, M. Angew. Chem., Int. Ed. 2013, 51, 13901.
[22] Lo, W. C.; Hunter, J. E.; Watson, G. B.; Patny, A.; Iyer, P. S.; Boruwa, J. US 9211280, 2015.
[23] Sun, F.; Zhan, Y. CN 108341814, 2018.

从α-三氟甲基苄溴合成烷基硫酸盐——脱卤亚磺化反应的延伸

Synthesis of Alkyl Sulfate from α-Trifluoromethylbenzylbromide—An Extension of Sulfinatodehalogenation

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