Recent Advances in Trifluoromethoxylation Reactions
- Corresponding author: Tang Pingping, ptang@nankai.edu.cn
Citation:
Wang Feng, Tang Pingping. Recent Advances in Trifluoromethoxylation Reactions[J]. Chinese Journal of Organic Chemistry,
;2020, 40(7): 1805-1813.
doi:
10.6023/cjoc202003048
(a) Becker A. Inventory of Industrial Fluoro-biochemicals, Eyrolles, Paris, 1996.
(b) Smart, B. E. J. Fluorine Chem. 2001, 109, 3.
(c) Dunitz, J. D. ChemBioChem 2004, 5, 614.
(d) Dolbier, W. R. J. Fluorine Chem. 2005, 126, 157.
(e) Hird, M. Chem. Soc. Rev. 2007, 36, 2070.
(f) Pagliaro, M.; Ciriminna R. J. Mater. Chem. 2005, 15, 4981.
(g) Wang, J.; Snchez-Rosell, M.; AceÇa, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
(h) Jeschke, P. ChemBioChem 2004, 5, 570.
(a) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
(b) Mller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
Leo, A.; Hansch, C.; Elkins, D. Chem. Rev. 1971, 71, 525.
doi: 10.1021/cr60274a001
Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
doi: 10.1021/cr00002a004
(a) Kapustin, E. G.; Bzhezovsky, V. M.; Yagupolskii, L. M. J. Fluorine Chem. 2002, 113, 227.
(b) Klocker, J.; Karpfen, A.; Wolschann, P. Chem. Phys. Lett. 2003, 367, 566.
(c) Manteau, B.; Genix, P.; Brelot, L.; Vors, J. P.; Pazenok, S.; Giornal, F.; Leuenberger, C.; Leroux, F. R. Eur. J. Org. Chem. 2010, 6043.
(a) Yagupol'skii, L. M. Dokl. Akad. Nauk SSSR 1955, 105, 100.
(b) Yarovenko, N. N.; Vasileva, A. S. Zh. Obshch. Khim. 1958, 28, 2502.
(c) Yagupol'skii, L. M.; Troitskaya, V. I. J. Gen. Chem. USSR 1961, 31, 845.
(d) Yagupol'skii, L. M.; Orda, V. V. Zh. Obshch. Khim. 1964, 34, 1979.
(e) Manteau, B.; Genix, P.; Brelot, L.; Vors, J. P.; Pazenok, S.; Giornal, F.; Leuenberger, C.; Leroux, F. R. Eur. J. Org. Chem. 2010, 6043.
(f) Sheppard, W. A. J. Org. Chem. 1964, 29, 1.
(g) Kuroboshi, M.; Suzuki, K.; Hiyama, T. Tetrahedron Lett. 1992, 33, 4173.
(h) Kanie, K.; Tanaka, Y.; Suzuki, K.; Kuroboshi, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 471.
(i) Kuroboshi, M.; Hiyama, T. Adv. Synth. Catal. 2001, 343, 235.
For recent reviews on trifluoromethoxylation reactions, see: (a) Besset, T.; Jubault, P.; Pannecouke, X.; Poisson, T. Org. Chem. Front. 2016, 3, 1004.
(b) Tlili, A.; Toulgoat, F.; Billard, T. Angew. Chem., Int. Ed. 2016, 57, 11726.
(c) Lee, K. N.; Lee, J. W.; Ngai, M. Y. Tetrahedron 2018, 74, 7127.
(d) Lee, J. W.; Lee, K. N.; Ngai, M. Y. Angew. Chem., Int. Ed. 2019, 58, 11171.
(e) Hardy, M. A.; Chachignon, H.; Cahard, D. Asian J. Org. Chem. 2019, 8, 591.
(f) Zhang, X. F.; Tang, P. P. Sci. China: Chem. 2019, 62, 525.
(g) Jiang, X. H.; Tang, P. P. Chin. J. Chem. 2020, 38, 101.
(a) Umemoto, T.; Adachi, K.; Ishihara, S. J. Org. Chem. 2007, 72, 6905.
(b) Stanek, K.; Koller, R.; Togni, A. J. Org. Chem. 2008, 73, 7678.
(c) Liang, A.; Han, S.; Liu, Z.; Wang, L.; Li, J.; Zou, D.; Wu, Y. Chem.-Eur. J. 2016, 22, 5102.
(d) Koller, R.; Huchet, Q.; Battaglia, P.; Welch, J. M.; Togni, A. Chem. Commun. 2009, 5993.
(e) Santschi, N.; Geissbhler, P.; Togni, A. J. Fluorine Chem. 2012, 135, 83.
(f) Matousek, V.; Pietrasiak, E.; Sigrist, L.; Czarniecki, B.; Togni, A. Eur. J. Org. Chem. 2014, 3087.
(g) Hojczyk, K. N.; Feng, P.; Zhan, C.; Ngai, M. Y. Angew. Chem., Int. Ed. 2014, 53, 14559.
(h) Chu, L.; Qing, F. L. Acc. Chem. Res. 2014, 47, 1513.
(i) Liu, J. B.; Chen, C.; Chu, L.; Chen, Z. H.; Xu, X. H.; Qing, F. L. Angew. Chem., Int. Ed. 2015, 54, 11839. (j) Liu, J. B.; Xu, X. H.; Qing, F. L. Org. Lett. 2015, 17, 5048.
(k) Naumann, D.; Kischkewitz, J. J. Fluorine Chem. 1990, 46, 265.
(l) Hojczyk, K. N.; Feng, P.; Zhan, C.; Ngai, M. Y. Angew. Chem., Int. Ed. 2014, 53, 14559.
(m) Lee, K. N.; Lee, J. W.; Ngai, M. Y. Synlett 2016, 27, 313.
Kellogg, K. B.; Cady, G. H. J. Am. Chem. Soc. 1948, 70, 3986.
doi: 10.1021/ja01192a006
Venturini, F.; Navarrini, W.; Famulari, A.; Sansotera, M.; Dardani, P.; Tortelli, V. J. Fluorine Chem. 2012, 140, 43.
doi: 10.1016/j.jfluchem.2012.04.008
(a) Zheng, W. J.; Morales-Rivera, C. A.; Lee, J. W.; Liu, P.; Ngai, M. Y. Angew. Chem., Int. Ed. 2018, 57, 9645.
(b) Zheng, W. J.; Lee, J. W.; Morales-Rivera, C. A.; Liu, P.; Ngai, M. Y. Angew. Chem., Int. Ed. 2018, 57, 13795.
Jelier, B. J.; Tripet, P. F.; Pietrasiak, E.; Franzoni, I.; Jeschke, G.; Togni, A. Angew. Chem., Int. Ed. 2018, 57, 13784.
(a) Noftle, R. E.; Cady, G. H. Inorg. Chem, 1965, 4, 1010.
(b) Katsuhara, Y.; DesMarteau, D. D. J. Am. Chem. Soc. 1980, 102, 2681.
(a) Kolomeitsev, A. A.; Vorobyev, M.; Gillandt, H. Tetrahedron Lett. 2008, 49, 449.
(b) Ignatyev, N.; Hierse, W.; Seidel, M.; Bathe, A.; Schroeter, J.; Koppe, K.; Meier, T.; Barthen, P.; Frank, W. DE 102008024221, 2009.
(c) Ignatyev, N.; Hierse, W.; Seidel, M.; Bathe, M.; Schroeter, J.; Koppe, K.; Meier, T.; Barthen, P.; Frank, W. WO 2009141053, 2009.
(d) Marrec, O.; Billard, T.; Vors, J. P.; Pazenok, S.; Langlois, B. R. J. Fluorine Chem. 2010, 131, 200.
(e) Sokolenko, T. M.; Davydova, Y. A.; Yagupol'skii, Y. L. J. Fluorine Chem. 2012, 136, 20.
(a) Barbion, J.; Pazenok, S.; Vors, J. P.; Langlois, B. R.; Billard, T. Org. Process Res. Dev. 2014, 18, 1037.
(b) Chen, C. H.; Chen, P. H.; Liu, G. S. J. Am. Chem. Soc. 2015, 137, 15648.
(c) Chen, C. H.; Luo, Y. X.; Fu, L.; Chen, P. H.; Lan, Y.; Liu, G. S. J. Am. Chem. Soc. 2018, 140, 1207.
(d) Chen, S.; Huang, Y.; Fang, X.; Li, H.; Zhang, Z.; Hor, T. S. A.; Weng, Z. Dalton Trans. 2015, 44, 19682.
(e) Zha, G. F.; Han, J. B.; Hu, X. Q.; Qin, H. L.; Fang, W. Y.; Zhang, C. P. Chem. Commun. 2016, 52, 7458.
(f) Chen, D.; Lu, L.; Shen, Q. L. Org. Chem. Front. 2019, 6, 1801.
(g) Yang, Y.; Yao, J.; Yan, W.; Luo, Z.; Tang, Z. Org. Lett. 2019, 21, 8003.
(h) Chen, C. H.; Hou, C. Q.; Chen, P. H.; Liu, G. S. Chin. J. Chem. 2020, 38, 346.
(a) Qi, X. X.; Chen, P. H.; Liu, G. S. Angew. Chem., Int. Ed. 2017, 56, 9517.
(b) Chen, C. H.; Pfluger, P. M.; Chen, P. H.; Liu, G. S. Angew. Chem., Int. Ed. 2019, 58, 2392.
(a) Farnham, W. B.; Smart, B. E.; Middleton, W. J.; Calabrese, J. C.; Dixon, D. A. J. Am. Chem. Soc. 1985, 107, 4565.
(b) Huang, C.; Liang, T.; Harada, S.; Lee, E.; Ritter, T. J. Am. Chem. Soc. 2011, 133, 13308.
Newton, J. J.; Jilier, B. J.; Meanwell, M.; Martin, R. E.; Britton, R.; Friesen, C. M. Org. Lett. 2020, 22, 1785.
doi: 10.1021/acs.orglett.0c00099
Marrec, O.; Billard, T.; Vors, J.; Pazenok, P.; Langlois, B. R. Adv. Synth. Catal. 2010, 352:2831.
doi: 10.1002/adsc.201000488
(a) Guo, S.; Cong, F.; Guo, R.; Wang, L.; Tang, P P. Nat. Chem. 2017, 9, 546.
(b) Jiang, X. H.; Deng, Z. J.; Tang, P. P. Angew. Chem., Int. Ed. 2018, 130, 298.
(c) Liu, J.; Wei, Y. L.; Tang, P. P. J. Am. Chem. Soc. 2018, 140, 15194.
(d) Cong, F.; Wei, Y. L.; Tang, P. P. Chem. Commun. 2018, 54, 4473.
(e) Yang, H. D.; Wang, F.; Jiang, X. H.; Zhou, Y.; Xu, X. F.; Tang, P. P. Angew. Chem., Int. Ed. 2018, 57. 13266.
(f) Wang, F.; Xu, P.; Cong, F.; Tang, P. P. Chem. Sci. 2018, 9, 8836.
(g) Yang, S. Q.; Chen, M.; Tang, P. P. Angew. Chem., Int. Ed. 2019, 58, 7840.
Zhou, M.; Ni, C.; Zeng, Y.; Hu, J. B. J. Am. Chem. Soc. 2018, 140, 6801.
doi: 10.1021/jacs.8b04000
Li. Y.; Yang, Y.; Xin, J. R.; Tang, P. P. Nat. Commun. 2020, 11, 755.
doi: 10.1038/s41467-020-14598-1
Xu, P.; Guo, S.; Wang, L. Y.; Tang, P. P. Angew. Chem., Int. Ed. 2014, 53, 5955.
doi: 10.1002/anie.201400225
Xu, P.; Wang, F.; Fan, G. L.; Xu, X. F.; Tang, P. P. Angew. Chem., Int. Ed. 2017, 56, 1101.
Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
Shahua Huang , Xiaoming Guo , Lin Lin , Guangping Chang , Sheng Han , Zuxin Zhou . Application of “Integration of Industry and Education” in Engineering Chemistry: Improvement of the Pesticide Fipronil Production. University Chemistry, 2024, 39(3): 199-204. doi: 10.3866/PKU.DXHX202309064
Bing LIU , Huang ZHANG , Hongliang HAN , Changwen HU , Yinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO2 mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398
Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
Wanmin Cheng , Juan Du , Peiwen Liu , Yiyun Jiang , Hong Jiang . Photoinitiated Grignard Reagent Synthesis and Experimental Improvement in Triphenylmethanol Preparation. University Chemistry, 2024, 39(5): 238-242. doi: 10.3866/PKU.DXHX202311066
Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
Zhiqiang Hao , Jinyue Li , Shiqi Zhang , Yujia Hou , Helue Sun . 维生素B2促进的光催化氧化合成二苯甲酮. University Chemistry, 2026, 41(5): 350-357. doi: 10.12461/PKU.DXHX202510080
Fangfang Tan , Lele Zhang , Penghua Jing , Pengju Zhao , Yang Li . 烯烃光催化氧化制备二苯甲酮——介绍一个绿色合成综合实验. University Chemistry, 2026, 41(8): 380-388. doi: 10.12461/PKU.DXHX202507049
Haolin Yang , Aoxiang Fan , Yi Song , Yang Chen . 基于甲酰化-共轭脱氢串联策略的苯并呋喃-5-甲醛的制备——推荐一个基础有机合成综合性教学实验. University Chemistry, 2026, 41(5): 141-148. doi: 10.12461/PKU.DXHX202511156
Chenxu Gong , Weizhen Wang , Ruiying Zhang , Wenfeng Wang , Yuanming Li , Yaofeng Yuan , Keyin Ye . Computational Chemistry-Assisted Organic Structure Analysis (CCAOSA): A Case Study of Propeller-Shaped Hexabenzotriphenylene. University Chemistry, 2026, 41(4): 438-446. doi: 10.12461/PKU.DXHX202503076
Yajin Li , Huimin Liu , Lan Ma , Jiaxiong Liu , Dehua He . Photothermal Synthesis of Glycerol Carbonate via Glycerol Carbonylation with CO2 over Au/Co3O4-ZnO Catalyst. Acta Physico-Chimica Sinica, 2024, 40(9): 2308005-0. doi: 10.3866/PKU.WHXB202308005
Zhimin Sun , Wenyu Xue , Shuangshuang Yang , Chaoyang Zhang , Bo Yu , Xingwei Wang , Qiangliang Yu , Feng Zhou , Weimin Liu . Multifunctional coating for marine applications: simultaneously achieving corrosion resistance, microwave absorption, and drag reduction via fluorosilane-encapsulated CIPs. Acta Physico-Chimica Sinica, 2026, 42(11): 100292-0. doi: 10.1016/j.actphy.2026.100292
Tao Cao , Fang Fang , Nianguang Li , Yinan Zhang , Qichen Zhan . Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates. University Chemistry, 2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098
Shuting KONG , Fengshi ZHANG , Zhiyi LU , Yanling LIU , Minglang YE , Zhengfang HU , Longsheng WANG , Bing HU , Haiying WANG . Research advance of the preparation of tributyl citrate catalyzed by supported heteropolyacid catalysts. Chinese Journal of Inorganic Chemistry, 2026, 42(3): 441-452. doi: 10.11862/CJIC.20250303
Jian Jin , Jing Cheng , Xueping Yang . Integration Practice of Organic Chemistry Experiment and Safety Education: Taking the Synthesis of Triphenylmethanol as an Example. University Chemistry, 2024, 39(3): 345-350. doi: 10.3866/PKU.DXHX202309010
Chengxiao Zhao , Zhaolin Li , Dongfang Wu , Xiaofei Yang . SBA-15 templated covalent triazine frameworks for boosted photocatalytic hydrogen production. Acta Physico-Chimica Sinica, 2026, 42(1): 100149-0. doi: 10.1016/j.actphy.2025.100149
Qiaorong RU . Synthesis and characterization of tripyridine functionalized polyionic liquid luminescent materials. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 111-119. doi: 10.11862/CJIC.20250121
Junjie Zhang , Jinke Li , Chaochao Dong , Jiawen Guo , Yue Wang , Yingxin Shui . 数字化技术在共轭聚合物探针检测全氟烷基化合物中的应用——微观机理探究与可视定量分析. University Chemistry, 2026, 41(10): 226-238. doi: 10.12461/PKU.DXHX202509092
Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
Vanita Vanita , Roland Schoch , Pascal Puphal , Hasan Yilmaz , Matthias Bauer , Oliver Clemens . Structural and electrochemical behaviour of bilayer manganite LaSr2Mn2O6.96 cathode for all-solid-state fluoride ion batteries. Acta Physico-Chimica Sinica, 2026, 42(3): 100181-0. doi: 10.1016/j.actphy.2025.100181