以三氟乙酸及其衍生物为三氟甲基源的三氟甲基化反应研究进展

doi:10.6023/cjoc201810033

摘要/Abstract

含有三氟甲基基团的有机分子中常常表现出独特的物理和化学性质，具有非常广泛的应用.三氟乙酸及其衍生物具有廉价、易得、稳定等优点，并且反应的副产物是二氧化碳，是理想的三氟甲基化试剂，具有广阔的应用前景.综述了以三氟乙酸及其衍生物为三氟甲基源的三氟甲基化反应的最新研究进展，主要包括C-X （X=Br，I）键、C-H键，C=X （X=C，O）的三氟甲基化反应，对反应的相关机理进行了论述.

关键词: 三氟乙酸, 氟化学, 氟, 三氟乙基化, 碳氢键活化

Organic molecules containing trifluoromethyl groups often exhibit unique physical and chemical properties, and have found extensive applications. Trifluoroacetic acid and its derivatives have advantages including low cost, ready availability and high stability. Furthermore, CO₂ is the byproduct. Therefore, trifluoroacetic acid and its derivatives are ideal trifluoromethylating reagents, and have great application potentials. The progress of trifluoromethylation reactions using trifluoroacetic acid and its derivatives as CF₃-sources is reviewed, including the reactions of C-X (X=Br and I), C-H, and C=X (X=C, O). The mechanisms are also introduced.

Key words: trifluoroacetic acid, CF₃-sources, trifluoromethylation reaction, C-H activation

引用此文

季小明, 史广法, 张扬会. 以三氟乙酸及其衍生物为三氟甲基源的三氟甲基化反应研究进展[J]. 有机化学, 2019, 39(4): 929-939.

Ji Xiaoming, Shi Guangfa, Zhang Yanghui. Progress of Trifluoromethylation Using Trifluoroacetic Acid and Its Derivatives as CF₃-Sources[J]. Chin. J. Org. Chem., 2019, 39(4): 929-939.

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参考文献

[1] (a) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
(b) Li, Y.; Wu, Y.; Li, G.-S.; Wang, X.-S. Adv. Synth. Catal. 2014, 356, 1412.
[2] Jeschke, P. ChemBioChem 2004, 5, 570.
[3] (a) O'Hagan, D.; Harper, D. B. J. Fluorine Chem. 1999, 100, 127.
(b) Vaillancourt, F. H.; Yeh, E.; Vosburg, D. A.; GarneauTsodikova, S.; Walsh, C. T. Chem. Rev. 2006, 106, 3364.
[4] (a) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
(b) Schlosser, M. Angew. Chem., Int. Ed. 2006, 45, 5432.
[5] Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
[6] (a) Ismail, F. M. D. J. Fluorine Chem. 2002, 118, 27.
(b) Bégué, J.-P.; Bonnet-Delpon, D. J. Fluorine Chem. 2006, 127, 992.
(c) Petrov, V. A. Fluorinated Heterocyclic Compounds:Synthesis, Chemistry, and Applications, John Wiley & Sons, Inc, Hoboken, NJ, USA, 2009.
(d) Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology, John Wiley & Sons, Ltd, Chichester, UK., 2009.
(e) Zhu, W.; Wang, J.; Wang, S. J. Fluorine Chem. 2014, 167, 37.
(f) Zhang, J.; Jin, C.; Zhang, Y. Chin. J. Org. Chem. 2014, 34, 662(in Chinese). (张霁, 金传飞, 张英俊, 有机化学, 2014, 34, 662.)
[7] (a) Penning, T. D.; Talley, J. J.; Bertenshaw, S.R.; Carter, J. S.; Collins, P. W.; Docter, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.; Perkins, W. E.; Seibert, K. A.; Veenhuizen, W. Y.; Zhang, Y.; Isakson, P.C. J. Med. Chem. 1997, 40, 1347.
(b) Chakraborti, A. K.; Garg, S. K.; Kumar, R.; Motiwala, H. F.; Jadhavar, P. S. Curr. Med. Chem. 2010, 17, 1563.
[8] (a) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
(b) Prakash, S. G. K.; Yudin, A. K. Chem. Rev. 1997, 97, 757.
[9] (a) Ye, Y.; Ball, N. D.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 14682.
(b) Wang, X.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648.
(c) Zhang, X.; Dai, H.; Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2012, 134, 11948.
(d) Mu, X.; Chen, S.; Zhen, X.; Liu, G. Chem.-Eur. J. 2011, 17, 6039.
(e) Zhang, L.-S.; Chen, K.; Chen, G.; Li, B.-J.; Luo, S.; Guo, Q.-Y.; Wei, J.-B.; Shi, Z.-J. Org. Lett. 2013, 15, 10.
(f) Miura, M.; Feng, C.-G.; Ma, S.; Yu, J.-Q. Org. Lett. 2013, 15, 5258.
(g) Culkin, D. A.; Hartwig, J. F. Organometallics 2004, 23, 3398.
(h) Grushin, V. V. Acc. Chem. Res. 2010, 43, 160.
(i) Hughes, R. P.; Meyer, M. A.; Tawa, M. D.; Ward, A. J.; Williamson, A.; Rheingold, A. L.; Zakharov, L. N. Inorg. Chem. 2004, 43, 747.
(j) Ball, N. D.; Gary, J. B.; Ye, Y.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 7577.
(k) Ball, N. D.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 2878.
(l) Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679.
[10] (a) Shimizu, R.; Egami, H.; Nagi, T.; Chae, J.; Hamashima, Y.; Sodeoka, M. Tetrahedron Lett. 2011, 51, 5947.
(b) Zhang, C.-P.; Wang, Z.-L.; Chen, Q.-Y.; Zhang, C.-T.; Gu, Y.-C.; Xiao, J.-C. Angew. Chem., Int. Ed. 2011, 50, 1896.
(c) Liu, T.; Shen, Q. Org. Lett. 2016, 13, 2342.
(d) Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2012, 134, 1298.
(e) Cai, S.; Chen, C.; Sun, Z.; Xi, C. Chem. Commun. 2013, 49, 4552.
(f) He, Z.; Tan, P.; Hu, J. Org. Lett. 2016, 18, 72.
(g) Li, X.; Zhao, J.; Zhang, L.; Hu, M.; Wang, L.; Hu J. Org. Lett. 2015, 17, 298.
(h) Gao, X.; Xiao, Y.-L.; Wan, X.; Zhang X. Angew. Chem., Int. Ed. 2018, 57, 3187.
(i) Xu, X.; Chen, H.; He, J.; Xu, H. Chin. J. Chem. 2017, 35, 1665.
[11] (a) Hafner, A.; Stefan, B. Angew. Chem., Int. Ed. 2012, 51, 3713.
(b) Ye, Y.; Lee, S. H.; Sanford, M. S. Org. Lett. 2011, 13, 5464.
(c) Loy, R. N.; Sanford, M. S. Org. Lett. 2011, 13, 2548.
(d) Seo, S.; Taylor, J. B.; Greaney, M. F. Chem. Commun. 2013, 49, 6385.
(e) Liu, Y.-R.; Tu, H.-Y.; Zhang, X.-G. Synthesis 2015, 47, 3460.
[12] Kino, T.; Nagase, Y.; Ohtsuka, Y.; Yamamoto, K.; Uraguchi, D.; Tokuhisa, K.; Yamakawa, T. J. Fluorine Chem. 2010, 131, 98.
[13] (a) Nagib, D. A.; MacMillan, D. W. C. Nature 2011, 480, 224.
(b) Iqbal, N.; Choi, S.; Ko, E.; Cho, E. J. Tetrahedron Lett. 2012, 53, 2005.
(c) Kamigata, N.; Fukushima, T.; Yoshida, M. Chem. Lett. 1990, 649.
(d) Kamigata, N.; Ohtsuka, T.; Fukushima, T.; Yoshida, M.; Shimizu, T. J. Chem. Soc. Perkin Trans. 11994, 1339.
(e) Xie, J.; Yuan, X.; Abdukader, A.; Zhu, C.; Ma, J. Org. Lett. 2014, 16, 1768.
[14] Mejía, E.; Togni, A. ACS Catal. 2012, 2, 521.
[15] (a) Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8950.
(b) Parsons, A. T.; Buchwald, S. L. Nature 2011, 480, 184.
[16] (a) Ji, Y.; Brueckl, T.; Baxter, R. D.; Fujiwara, Y.; Seiple, I. B.; Su, S.; Blackmond, D. G.; Baran, P. S. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 14411.
(b) Fujiwara, Y.; Dixon, J. A.; O'Hara, F.; Funder, E. D.; Dixon, D. D.; Rodriguez, R. A.; Baxter, R. D.; Herle, B.; Sach, N.; Collins, M. R.; Ishihara, Y.; Baran, P. S. Nature 2012, 492, 95.
(c) Wu, X.; Chu,L.; Qing, F.-L. Tetrahedron Lett. 2013, 54, 249.
(d) Yang, Y.-D.; Iwamoto, K.; Tokunaga, E.; Shibata, N. Chem. Commun. 2013, 49, 5510.
(e) Fennewald, J. C.; Lipshutz, B. H. Green Chem. 2014, 16, 1097.
(f) Cui, L.; Matusaki, Y.; Tada, N.; Miura, T.; Uno, B.; Itoh, A. Adv. Synth. Catal. 2013, 355, 2203.
[17] (a) Umemoto, T. Chem. Rev. 1996, 96, 1757.
(b) Prakash, G. K. S.; Hu, J. Acc. Chem. Res. 2007, 40, 921.
(c) Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757.
(d) Shibata, N.; Matsnev, A.; Cahard, D. Beilstein J. Org. Chem. 2010, 6, 65.
(e) Chu, L.; Qing, F.-L. Acc. Chem. Res. 2014, 47, 1513.
[18] Shi, G.; Shao, C.; Pan, S.; Yu, J.; Zhang, Y. Org. Lett. 2015, 17, 38.
[19] (a) Lopez, S. E.; Salazar, J. J. Fluorine Chem. 2013, 156, 73.
(b) Rui, S.; Lei, L. Sci. China Chem. 2011, 54, 1670.
(c) Rodríguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030.
[20] 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.
[21] Matsui, K.; Tobita, E.; Ando, M.; Kondo, K. Chem. Lett. 1981, 12, 1719.
[22] Hünig, S.; Bau, R.; Kemmer, M.; Meixner, H.; Metzenthin, T.; Peters, K.; Sinzger, K.; Gulbis, J. Eur. J. Org. Chem. 1998, 2, 335.
[23] Austin, N. E.; Avenell, K. Y.; Boyfield, I.; Branch, C. L.; Hadley, M. S.; Jeffrey, P.; Johnson, C. N.; Macdonald, G. J.; Nash, D. J.; Riley, G. J.; Smith, A. B.; Stemp, G.; Thewlis, K. M.; Vong, A. K. K.; Wood, M. D. Bioorg. Med. Chem. Lett. 2001, 11, 685.
[24] Langlois, B. R.; Roques, N. J. Fluorine Chem. 2007, 128. 1318.
[25] McReynolds, K. A.; Lewis, R. S.; Ackerman, L. K. G.; Dubinina, G. G.; Brennessel, W. W.; Vicic, D. A. J. Fluorine Chem. 2010, 131, 1108.
[26] Li, Y.; Chen, T.; Wang, H.; Zhang, R.; Jin, K.; Wang, X.; Duan, C. Synlett 2011, 1713.
[27] Schareina, T.; Wu, X.-F.; Zapf, A.; Cotte, A.; Gotta, M.; Beller, M. Top Catal. 2012, 55, 426.
[28] Chen, M.; Buchwald, S. L. Angew. Chem., Int. Ed. 2013, 52, 11628.
[29] Maleckis, A.; Sanford, M. S. Organometallics 2014, 33, 2653.
[30] Lin, X.; Hou, C.; Li, H.; Weng, Z. Chem.-Eur. J. 2016, 22, 2075.
[31] Torikai, K.; Koga, R.; Liu, X.; Umehara, K.; Kitano, T.; Watanabe, K.; Oishi, T.; Noguchi, H.; Shimohigashi, Y. Bioorg. Med. Chem. 2017, 25, 5216.
[32] (a) Giri, R.; Shi, B.-F.; Engle, K. M.; Maugel, N.; Yu, J.-Q. Chem. Soc. Rev. 2009, 38, 3242.
(b) Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293.
(c) Liu, C.; Yuan, J.; Gao, M.; Tang, S.; Li, W.; Shi, R.; Lei, A. Chem. Rev. 2015, 115, 12138.
(d) Song, G.; Li, X. Acc. Chem. Res. 2015, 48, 1007.
(e) Guo, X.-X.; Gu, D.-W.; Wu, Z.; Zhang, W. Chem. Rev. 2015, 115, 1622.
(f) Zheng, C.; You, S.-L. RSC Adv. 2014, 4, 6173.
(g) Ackermann, L. Chem. Rev. 2011, 111, 1315.
(h) Neufeldt, S. R.; Sanford, M. S. Acc. Chem. Res. 2012, 45, 936.
(i) Zhang, Y.; Shi, G.; Yu, J.-Q. Carbon-Carbon σ-Bond Formation via C-H Bond Functionalization in Comprehensive Organic Synthesis, 2nd ed., Vol. 3, Eds.:Molander, G.; Knochel, P., Elsevier, Oxford, 2014, pp. 1101~1209.
[33] Grinberg, V. A.; Polishchuk, V. R.; German, L. S.; Kanevskii, L. S.; Vassiliev, Y. B. Izv. Akad. Nauk SSSR, Ser. Khim. 1978, 3, 673.
[34] Sawada, H.; Nakayama, M.; Yoshida, M.; Yoshida, T.; Kamigata, N. J. Fluorine Chem. 1990, 46, 423.
[35] Lai, C.; Mallouk, T. E. J. Chem. Soc., Chem. Commun. 1993, 17, 1359.
[36] Matsui, M.; Kondoh, S.; Shibata, K.; Muramatsu, H. Bull. Chem. Soc. Jpn. 1995, 68, 1042.
[37] Tanabe, Y.; Matsuo, N.; Ohno, N. J. Org. Chem. 1988, 53, 4583.
[38] Depecker, C.; Marzouk, H.; Trevin, S.; Devynck, J. New J. Chem. 1999, 23, 739.
[39] Beatty, J. W.; Douglas, J. J.; Cole, K. P.; Stephenson, C. R. J. Nat. Commun. 2015, 6, 7919.
[40] Zhong, S.; Hafner, A.; Hussal, C.; Nieger, M.; Brase, S. RSC Adv. 2015, 5, 6255.
[41] Lin, J.; Li, Z.; Kan, J.; Huang, S.; Su, W.; Li, Y. Nat. Commun. 2017, 8, 1.
[42] Yang, B.; Yu, D.; Xu, X.-H.; Qing, F.-L. ACS Catal. 2018, 8, 2839.
[43] (a) Parsons, A. T.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 9120.
(b) Xu, J.; Fu, Y.; Luo, D.-F.; Jiang, Y.-Y.; Xiao, B.; Liu, Z.-J.; Gong, T.-J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 15300.
(c) Wang, X.; Ye, Y.; Zhang, S.; Feng, J.; Xu, Y.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2011, 133, 16410.
(d) Liu, X.; Xiong, F.; Huang, X.; Xu, L.; Li, P.; Wu, X. Angew. Chem., Int. Ed. 2013, 52, 6962.
[44] Brookes, C. J.; Coe, P. L.; Owen, D. M.; Pedler, A. E.; Tatlow, J. C. J. Chem. Soc., Chem. Commun. 1974, 9, 323.
[45] Barton, D. H. R.; Lacher, B.; Zard, S. Z. Tetrahedron 1986, 42, 2325.
[46] Jablonski, L.; Joubert, J.; Billard, T.; Langlois, B. R. Synlett 2003, 230.
[47] Chang, Y.; Cai, C. J. Fluorine Chem. 2005, 126, 937.
[48] Arai, K.; Watts, K.; Wirth, T. ChemistryOpen 2014, 3, 23.
[49] Kawamura, S.; Sodeoka, M. Angew. Chem., Int. Ed. 2016, 55, 8740.
[50] Valverde, E.; Kawamura, S.; Sekine, D.; Sodeoka, M. Chem. Sci. 2018, 9, 7115.
[51] Zhang, Y.; Li, Z.; Song, H.; Wang, B. Chin. J. Chem. 2018, 36, 635.