Copper-Catalyzed Arylated Etherification of 2,2-Difluoroethanol and Its Mechanistic Study

doi:10.6023/cjoc202003035

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 2018-2025.DOI: 10.6023/cjoc202003035 Previous Articles Next Articles

铜催化二氟乙醇的芳基醚化反应及其机理研究

黄帅帅^a, 聂一雪^a, 杨晶晶^a, 郑战江^a, 曹建^a, 徐征^a, 徐利文^a,b

a 杭州师范大学有机硅化学及材料技术教育部重点实验室杭州 311121;
b 杭州师范大学氟硅精细化学品与材料制造协同创新中心杭州 311121

收稿日期:2020-03-14 修回日期:2020-04-17 发布日期:2020-04-23
通讯作者: 郑战江, 徐利文 E-mail:zzjiang78@hznu.edu.cn;liwenxu@hznu.edu.cn
基金资助:
国家自然科学基金（Nos.21703051，21801056）和杭州市科技局（No.20180432B05）资助项目.

Copper-Catalyzed Arylated Etherification of 2,2-Difluoroethanol and Its Mechanistic Study

Huang Shuaishuai^a, Nie Yixue^a, Yang Jingjing^a, Zheng Zhanjiang^a, Cao Jian^a, Xu Zheng^a, Xu Liwen^a,b

a Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121;
b Collaborative Innovation Center for Fluorosilicone-based Fine Chemicals and Materials, Hangzhou Normal University, Hangzhou 311121

Received:2020-03-14 Revised:2020-04-17 Published:2020-04-23
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21703051, 21801056) and the Hangzhou Science and Technology Bureau of China (No. 20180432B05).

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Abstract

Both organofluorine and organosilicon compounds are one of the most important types of high-tech product in elementorganic chemistry, and have been received much attetions in the past decades. Considering the imporatance of difluoroethanol moeity in pesticides, the development of a mild and efficient copper-catalyzed arylated etherification reaction of difluoroethanol is highly desirable. Herein, a mild and efficient method for the preparation of difluoroethyl aryl ethers was developed by the copper-catalyzed Ullmann-type arylated etherification reaction of aryl bromides or iodides with 2,2-difluoroethanol. This reaction proceeds smoothly in the presence of CuI and 8-hydroxyquinoline/t-BuOK, and has a broad substrate scope. ESI-MS analysis supported the existence of LCu(Ⅲ)Ar(OR) species during this catalytic reaction. Further density functional theory (DFT) calculations suggest a proposed mechanism of arylated etherification reaction involving oxidative addition, followed by nucleophile substitution and reductive elimination would be rational.

Key words: Ullmann reaction, Cu-catalyzed, fluorinated compound, DFT calculation, 8-hydroxyquinoline

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Huang Shuaishuai, Nie Yixue, Yang Jingjing, Zheng Zhanjiang, Cao Jian, Xu Zheng, Xu Liwen. Copper-Catalyzed Arylated Etherification of 2,2-Difluoroethanol and Its Mechanistic Study[J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2018-2025.

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[1] (a) Nakajima, T.; Groult, H. Fluorinated Materials for Energy Conversion, Elsevier, London, 2005.
(b) Wong, S.; Ma, H.; Jen, A. K. Y.; Barto, R.; Frank, C. W. Macromolecules 2003, 36, 8001.
(c) Wong, S.; Ma, H.; Jen, A. K. Y.; Barto, R.; Frank, C. W. Macromolecules 2004, 37, 5578.
[2] (a) Tressaud, A.; Haufe, G. Fluorine and Health:Molecular Imaging, Biomedical Materials and Pharmaceuticals, Elsevier, London, 2008.
(b) Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology, Wiley, Hoboken, 2009.
(c) Xu, X. H.; Matsuzaki, K.; Shibata, N. Chem. Rev. 2015, 115, 731.
[3] Jeschke, P. ChemBioChem 2004, 5, 570.
[4] (a) Banks, R. E.; Smart, B. E.; Tatlow, J. C. Organofluorine Chemistry, Principles and Commercial Applications, Plenum, New York, 1994.
(b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
(c) Wang, J.; Sanchez-Rosello, M.; Acena, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
[5] (a) Gao, X.; Cheng, R.; Xiao, Y. L.; Wan, X. L.; Zhang, X. G. Chem 2019, 5, 2987.
(b) Begue, J. P.; Bonnet-Delpon, D. J. Fluorine Chem. 2006, 127, 992.
(c) Cerqueira, N. M. F. S. A.; Fernandes, P. A.; Ramos, M. J. Chemistry 2007, 13, 8507.
(d) Teague, S. J. Drug Discovery Today 2011, 16, 398.
(e) Cheng, J. J.; Giguere, P. M.; Onajole, O. K.; Lv, W.; Gaisin, A.; Gunosewoyo, H.; Schmerberg, C.; Pogorelov, V. M.; Rodriguiz, R. M.; Vistoli, G.; Wetsel, W. C.; Roth, B. L.; Kozikowski, A. P. J. Med. Chem. 2015, 58, 1992.
(f) Johan, B. WO 2010132016, 2010.
(g) Gregory, B. M. WO 02072528, 2002.
(h) Gernert, D. L.; Ajamie, R.; Ardecky, R. A.; Bell, M. G.; Leibowitz, M. D.; Mais, D. A.; Mapes, C. M.; Michellys, P. Y.; Rungta, D.; Reifel-Miller, A.; Tyhonas, J. S.; Yumibe, N.; Grese, T. A. Bioorg. Med. Chem. Lett. 2003, 13, 3191.
(i) Ulrich, K. WO 2005085203, 2005. (j) Ulrich, K. WO 2006092417, 2006.
[6] (a) Irrupe, Jr. J.; Casas, J.; Messeguer, A. Bioorg. Med. Chem. Lett. 1993, 3, 179.
(b) Thomas, W. J.; Ronald, S. T. J. Agric. Food Chem. 2005, 53, 7179.
[7] (a) Schwan, G.; Asskar, G. B.; Hcfgen, N.; Kubicova, L.; Funke, U.; Egerland, U.; Zahn, M.; Nieber, K.; Scheunemann, M.; Strter, N.; Brust, P.; Briel, D. ChemMedChem 2014, 9, 1476.
(b) OShea, P. D.; Gauvreau, D.; Gosselin, F.; Hughes, G.; Nadeau, C.; Roy, A.; Scott Shultz, C. J. Org. Chem. 2009, 74, 4547.
(c) Kamal, A.; Pratap, T. B.; Ramana, K. V.; Ramana, A. V.; Babu, A. H. Tetrahedron Lett. 2002, 43, 7353.
(d) Camps, F.; Coll, J.; Messeguer, A.; Perics, M. A. Synthesis 1980, 727.
[8] Fuhrmann, E.; Talbiersky, J. Org. Process Res. Dev. 2005, 9, 206.
[9] (a) Zhang, H.; Ruiz-Castillo, P.; Buchwald, S. L. Org. Lett. 2018, 20, 1580.
(b) Gowrisankar, S.; Sergeev, A. G.; Anbarasan, P.; Spannenberg, A.; Neumann, H.; Beller, M. J. Am. Chem. Soc. 2010, 132, 11592.
(c) Sawatzky, R. S.; Hargreaves, B. K. V.; Stradiotto, M. Eur. J. Org. Chem. 2016, 2016, 2444.
(d) Dumrath, A.; Wu, X. F.; Neumann, H.; Spannenberg, A.; Jackstell, R.; Beller, M. Angew. Chem., Int. Chem. 2010, 49, 8988.
(e) Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224.
[10] Rangarajan, T. M.; Singh, R.; Brahma, R.; Devi, K.; Pal Singh, R.; Singh, R. P.; Prasad, A. K. Chem.-Eur. J. 2014, 20, 14218.
[11] (a) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459.
(b) Goodbrand, H. B.; Hu, N. X. J. Org. Chem. 1999, 64, 670.
(c) Fagan, P. J.; Hauptman, E.; Shapiro, R.; Casalnuovo, A. J. Am. Chem. Soc. 2000, 122, 5043.
[12] (a) Suzuki, H.; Matuoka, T.; Ohtsuka, I.; Osuka, A. Synthesis 1985, 499.
(b) Sugata, H.; Tsubogo, T.; Kino, Y.; Uchiro, H. Tetrahedron Lett. 2017, 58, 1015.
[13] (a) Wolter, M.; Nordmann, G.; Job, E.; Buchwald, S. L. Org. Lett. 2002, 4, 973.
(b) Tlili, A.; Xia, N.; Monnier, F.; Taillefer, M. Angew. Chem., Int. Chem. 2009, 48, 8725.
(c) Chen, Z. X.; Jiang, Y. W.; Zhang, L.; Guo, Y. L.; Ma, D. W. J. Am. Chem. Soc. 2019, 141, 3541.
(d) Cai, Q.; Zhou, W. Chin. J. Chem. 2020, 38, 879.
[14] (a) Huang, R. L.; Huang, Y. J.; Lin, X. X.; Rong, M.; Weng, Z. Angew. Chem., Int. Ed. 2015, 54, 5736.
(b) Vuluga, D.; Legros, J.; Crousse, B.; Bonnet-Delpon, D. Eur. J. Org. Chem. 2009, 3513.
[15] Niu, J. J.; Guo, P. R.; Kang, J. T.; Li, Z. G.; Xu, J. W.; Hu, S. J. J. Org. Chem. 2009, 74, 5075.
[16] (a) Qian, C.; Zhu, W.; Liu, J.; Wang, X.; Qiu, L. Chin. J. Org. Chem. 2019, 39, 1695(in Chinese). (钱存卫, 朱文倩, 刘俊龙, 王雪敏, 仇立干, 有机化学, 2019, 39, 1695.)
(b) Liu, X.; Chen, W.; Ni, B.; Chen, X.; Qian, C.; Ge, X. Chin. J. Org. Chem. 2018, 38, 1703(in Chinese). (刘学民, 陈雯, 倪邦庆, 陈新志, 钱超, 葛新, 有机化学, 2018, 38, 1703.)
(c) Hu, X.; Yang, B.; Yao, W.; Wang, D. Chin. J. Org. Chem. 2018, 38, 3296(in Chinese). (胡昕宇, 杨伯斌, 姚玮, 王大伟, 有机化学, 2018, 38, 3296.)
[17] (a) Ye, D.; Huang, R.; Zhu, H.; Zou, L.; Wang, D. Org. Chem. Front. 2019, 6, 62.
(b) Hu, W.; Zhang, Y.; Zhu, H.; Ye, D.; Wang, D. Green Chem. 2019, 21, 5345.
(c) Wang, D.; Zhao, K.; Xu, C.; Miao, H.; Ding, Y. ACS Catal. 2014, 4, 3910.
[18] (a) Johansson, C. C. C.; Colacot, T. J. Angew. Chem., Int. Ed. 2010, 49, 676.
(b) Cristau, H. J.; Cellier, P. P.; Spinddler, J. F.; Taillefer, M. Chem.- Eur. J. 2004, 10, 5607.
(c) Xie, X.; Cai, G.; Ma, D. Org. Lett. 2005, 7, 4693.
(d) Xie, X.; Chen, Y.; Ma, D. J. Am. Chem. Soc. 2006, 128, 16050.
[19] (a) Yu, H. Z.; Jiang, Y. Y.; Fu, Y.; Liu, L. J. Am. Chem. Soc. 2010, 132, 18078.
(b) Ribas, X.; Guell, I. Pure Appl. Chem. 2014, 86, 345.
(c) Jones, G. O.; Liu, P.; Houk, K. N.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 6205.
(d) Casitas, A.; Ribas, X. Chem. Sci. 2013, 4, 2301.
(e) Sambiagio, C.; Marsden, S. P.; Blacker, A. J.; McGowan, P. C. Chem. Soc. Rev. 2014, 43, 3525.
(f) Lefevre, G.; Franc, G.; Tlili, A.; Adamo, C.; Taillefer, M.; Ciofini, I.; Jutand, A. Organometallics 2012, 31, 7694.
(g) Giri, R.; Brusoe, A.; Troshin, K.; Wang, J. Y.; Font, M.; Hartwig, J. F. J. Am. Chem. Soc. 2018, 140, 793.
(h) Tye, J. W.; Weng, Z.; Giri, R.; Hartwig, J. F. Angew. Chem., Int. Ed. 2010, 49, 2185.

铜催化二氟乙醇的芳基醚化反应及其机理研究

Copper-Catalyzed Arylated Etherification of 2,2-Difluoroethanol and Its Mechanistic Study

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