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2018 , Vol. 38 >Issue 10: 2571 - 2589

DOI: https://doi.org/10.6023/cjoc201803045

综述与进展

过渡金属促进三氟甲基化反应的研究进展

  • 陈董涵 ,
  • 杨文 ,
  • 姚永祺 ,
  • 杨新 ,
  • 邓颖颍 ,
  • 杨定乔
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  • 华南师范大学化学与环境学院 教育部环境理论化学重点实验室 广州 510006

收稿日期: 2018-03-27

  修回日期: 2018-05-15

  网络出版日期: 2018-06-06

基金资助

国家自然科学基金（Nos.21172081，21372090）、广东省自然科学基金重点（No.S2013020013091）和广州市科技计划（No.201510010054）资助项目.

收起

Recent Advances in Transition Metal-Promoted Trifluoromethylation Reactions

  • Chen Donghan ,
  • Yang Wen ,
  • Yao Yongqi ,
  • Yang Xin ,
  • Deng Yingying ,
  • Yang Dingqiao
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  • Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou 510006

Received date: 2018-03-27

  Revised date: 2018-05-15

  Online published: 2018-06-06

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21172081, 21372090), the Natural Science Foundation of Guangdong Province (No. S2013020013091) and the City of Guangzhou Science and Technology Plan Projects (No. 201510010054).

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摘要

近年来，过渡金属促进三氟甲基化反应得到了快速发展.从促进三氟甲基化反应的过渡金属种类出发，综述了近几年来银、铁、钯、镍、铑和钴促进三氟甲基化反应的研究进展，并对部分反应可能的机理进行了讨论.

关键词： 过渡金属; 三氟甲基化; 研究进展

本文引用格式

陈董涵 , 杨文 , 姚永祺 , 杨新 , 邓颖颍 , 杨定乔 . 过渡金属促进三氟甲基化反应的研究进展[J]. 有机化学, 2018 , 38(10) : 2571 -2589 . DOI: 10.6023/cjoc201803045

Abstract

Recently, transition metal-promoted trifluoromethylation has been developed rapidly. Starting with the types of transition metal that promote the trifluoromethylation reactions, the research progress of trifluoromethylation promoted by silver, iron, palladium, nickel, rhodium and cobalt in recent years is reviewed. Moreover, the possible mechanisms of some parts of reactions are also discussed.

Key words： transition metal; trifluoromethylation; research progress

参考文献

[1] (a) Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305.
(b) Kirsch, P.; Bremer, M. Angew. Chem., Int. Ed. 2000, 39, 4216.
[2] Wong, D.-T.; Perry, K. W.; Bymaster, F. P. Nat. Rev. Drug. Discovery 2005, 4, 764.
[3] Margot, P.; Huggenberger, F.; Amrein, J.; Weiss, B. BCPC Conf.-Pests Dis. 1998, 2, 375.
[4] Reiffenrath, V.; Krause, J.; Plach, H. J.; Weber, G. Liq. Cryst. 1989, 5, 159.
[5] (a) Swarts, F. Bull. Acad. R. Belg. 1892, 24, 309.
(b) Boswell, G. A., Jr.; Ripka, W. C.; Scribner, R. M.; Tullock, C. W. Org. React. 1974, 21, 1.
[6] Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470.
[7] Lundgren, R. J.; Stradiotto, M. Angew. Chem., Int. Ed. 2010, 49, 9322.
[8] Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475.
[9] Roy, S.; Gregg, B. T.; Gribble, G. W.; Le, V. D. Tetrahedron Lett. 2011, 67, 2161.
[10] Wang, G.-Z.; He, X.-P.; Dai, J.-J.; Xu, H.-J. Chin. J. Org. Chem. 2014, 34, 837(in Chinese). (王光祖, 赫侠平, 戴建军, 许华建, 有机化学, 2014, 34, 837.)
[11] Lü, C.-P.; Shen, Q.-L.; Liu, D. Chin. J. Org. Chem. 2012, 32, 1380(in Chinese). (吕翠萍, 沈其龙, 刘丹, 有机化学, 2012, 32, 1380.)
[12] Qi, Z.-S.; Dong, Y.-L.; Li, Y.-M.; Duan, C.-Y. Prog. Chem. 2012, 24, 2178(in Chinese). (戚自松, 董亚丽, 李亚明, 段春迎, 化学进展, 2012, 24, 2178.)
[13] Pan, F.; Shi, Z.-J. Acta Chim. Sinica 2012, 70, 1679(in Chinese). (潘菲, 施章杰, 化学学报, 2012, 70, 1679.)
[14] Ye, Y.-D.; Lee, S. H.; Sanford, M. S. Org. Lett. 2011, 13, 5464.
[15] Han, J.-B.; Xu, B.; Hammond, G. B. Org. Lett. 2011, 13, 3450.
[16] Hafner, A.; Bräse, S. Angew. Chem., Int. Ed. 2012, 51, 3713.
[17] Wang, X.; Xu, Y.; Zhou, Y.-J.; Zhang, Y.; Wang, J.-B. Synthesis 2014, 46, 2143.
[18] Wu, X.-Y.; Chu, L.-L.; Qing, F.-L. Angew. Chem., Int. Ed. 2013, 52, 2198.
[19] Wang, K.-P.; Yun, S.-Y.; Mamidipalli, P.; Lee, D. Chem. Sci. 2013, 4, 3205.
[20] Zeng, Y.-W.; Zhang, L.-J.; Zhao, Y.-C.; Ni, C.-F.; Zhao, J.-W.; Hu, J.-B. J. Am. Chem. Soc. 2013, 135, 2955.
[21] Liu, Q.-L.; Wu, Y.-C.; Chen, P.-H.; Liu, G.-S. Org. Lett. 2013, 15, 6210.
[22] Wang, X.-B.; Qiu, G.-Y.-S.; Zhang, L.; Wu, J. Tetrahedron Lett. 2014, 55, 962.
[23] Yu, W.; Xu, X-H.; Qing, F-L. Adv. Synth. Catal. 2015, 357, 2039.
[24] SeO, S.; Taylor, J. B.; Greaney, M. F. Chem. Commun. 2013, 49, 6385.
[25] Teng, F.; Cheng, J.; Bolm, C. Org. Lett. 2015, 17, 3166.
[26] Liu, J.-B.; Xu, X.-H.; Qing, F.-L. Org. Lett. 2015, 17, 5048.
[27] Liu, J.-B.; Chen, C.; Chu, L.; Chen, Z.-H.; Xu, X.-H.; Qing, F.-L. Angew. Chem., Int. Ed. 2015, 54, 11839.
[28] Wu, Y.-B.; Lu, G.-P.; Yuan, T.; Xu, Z.-B.; Wan, L.; Cai, C. Chem. Commun. 2016, 52, 13668.
[29] Deb, A.; Manna, S.; Modak, A.; Patra, T.; Maity, S.; Maiti, D. Angew. Chem., Int. Ed. 2013, 52, 9747.
[30] Mai, W.-P.; Wang, J.-T.; Yang, L.-R.; Yuan, J.-W.; Xiao, Y.-M.; Mao, P.; Qu, L.-B. Org. Lett. 2014, 16, 204.
[31] Liu, J.-D.; Zhuang, S.-B.; Gui, Q.-W.; Chen, X.; Yang, Z.-Y.; Tan, Z. Eur. J. Org. Chem. 2014, 3196.
[32] Maji, A.; Hazra, A.; Maiti, D. Org. Lett. 2014, 16, 4524.
[33] Monir, K.; Bagdi, A. K.; Ghosh, M.; Hajra, A. J. Org. Chem. 2015, 80, 1332.
[34] Huang, P.; Li, Y.-M.; Fu, X.-M.; Zhang, R.; Jin, K.; Wang, W.-X.; Duan, C.-Y. Tetrahedron Lett. 2016, 57, 4705.
[35] Liu, Y.-R.; Tu, H.-Y.; Zhang, X.-G. Synthesis 2015, 47, 3460.
[36] Shi, G.-F.; Shao, C.-D.; Pan, S.-L.; Yu, J.-X.; Zhang, Y.-H. Org. Lett. 2015, 17, 38.
[37] Zhang, X.-M.; Wang, J.; Wan, Z.-H. Org. Lett. 2015, 17, 2086.
[38] Zhou, M.; Ni, C.-F.; He, Z.-B.; Hu, J.-B. Org. Lett. 2016, 18, 3754.
[39] Tan, X.-Q.; Liu, Z.-L.; Shen, H.-G.; Zhang, P.; Zhang, Z.-Z.; Li, C.-Z. J. Am. Chem. Soc. 2017, 139, 12430.
[40] Uraguchi, D.; Yamamoto, K.; Ohtsuka, Y.; Tokuhisa, K.; Yamakawa, T. Appl. Catal., A 2008, 342, 137.
[41] Kino, T.; Nagase, Y.; Ohtsuka, Y.; Yamamoto, K.; Uraguchi, D.; Tokuhisa, K.; Yamakawa, T. J. Fluorine Chem. 2010, 131, 98.
[42] Ohtsuka, Y.; Uraguchi, D.; Yamamoto, K.; Tokuhisa, K.; Yamakawa, T. J. Fluorine Chem. 2016, 181, 1.
[43] Parsons, A. T.; Senecal, T. D.; Buchwald, S. L. Angew. Chem., Int. Ed. 2012, 51, 2947.
[44] Egami, H.; Shimizu, R.; Usui, Y.; Sodeoka, M. Chem. Commun. 2013, 49, 7346.
[45] Yu, L.-Z.; Xu, Q.; Tang, X.-Y.; Shi, M. ACS Catal. 2016, 6, 526.
[46] Rey-Rodriguez, R.; Retailleau, P.; Bonnet, P.; Gillaizeau, I. Chem.-Eur. J. 2015, 21, 3572.
[47] Ma, J.-J.; Yi, W.-B.; Lu, G.-P.; Cai, C. Adv. Synth. Catal. 2015, 357, 3447.
[48] Li, Z.-R.; Bao, X.-X.; Sun, J.; Shen, J.; Wu, D.-Q.; Liu, Y.-K.; Deng, Q.-H.; Liu, F. Org. Chem. Front. 2016, 3, 934.
[49] Patra, T.; Deb, A.; Manna, S.; Sharma, U.; Maiti, D. Eur. J. Org. Chem. 2013, 2013, 5247.
[50] Yang, B.; Xu, X.-H.; Qing, F.-L. Chin. J. Chem. 2016, 34, 465.
[51] Klein, J. E. M. N.; Rommel, S.; Plietker, B. Organometallics 2014, 33, 5802.
[52] Exner, B.; Bayarmagnai, B.; Jia, F.; Goossen, L. J. Chem.-Eur. J. 2015, 21, 17220.
[53] Culkin, D. A.; Hartwig, J. F. Organometallics 2004, 23, 3398.
[54] Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2006, 128, 4632.
[55] Ball, N. D.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 2878.
[56] Cho, E. J.; Buchwald, S. L. Org. Lett. 2011, 13, 6552.
[57] Mu, X.; Wu, T.; Wang, H.-Y.; Guo, Y.-L.; Liu, G.-S. J. Am. Chem. Soc. 2012, 134, 878.
[58] Mu, X.; Chen, S.-J.; Zhen, X.-L.; Liu, G.-S. Chem.-Eur. J. 2011, 17, 6039.
[59] Samant, B. S.; Kabalka, G. W. Chem. Commun. 2011, 47, 7236.
[60] Yu, Y.-Y.; Ranade, A. R.; Georg, G. I. Adv. Synth. Catal. 2014, 356, 3510.
[61] Wang, X.-S.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648.
[62] Zhang, L.-S.; Chen, K.; Chen, G.-H.; Li, B.-J.; Luo, S.; Guo, Q.-Y.; Wei, J.-B.; Shi, Z.-J. Org. Lett. 2013, 15, 10.
[63] Zhang, X.-G.; Dai, H.-X.; Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2012, 134, 11948.
[64] Miura, M.; Feng, C.-G.; Ma, S.; Yu, J.-Q. Org. Lett. 2013, 15, 5258.
[65] Liu, C.; Chen, Q.-Y. Eur. J. Org. Chem. 2005, 3680
[66] Cho, E. J.; Senecal, T. D.; Kinzel, T.; Zhang, Y.; Watson, D. A.; Buchwald, S. L. Science 2010, 328, 1679.
[67] Natte, K.; Jagadeesh, R. V.; He, L.; Rabeah, J.; Chen, J.-B.; Taeschler, C.; Ellinger, S.; Zaragoza, F.; Neumann, H.; Brückner, A.; Beller, M. Angew. Chem., Int. Ed. 2016, 55, 2782.
[68] Li, Z.-D.; García-Domínguez, A.; Nevado, C. J. Am. Chem. Soc. 2015, 137, 11610.
[69] Yu, J.-P.; Yang, H.-J.; Fu, H. Adv. Synth. Catal. 2014, 356, 3669.
[70] Xu, J.; Qiao, L.; Shen, J.-B.; Chai, K.-J.; Shen, C.; Zhang, P.-F. Org. Lett. 2017, 19, 5661.
[71] Wu, Y.; Zhang, H.-R.; Jin, R.-X.; Lan, Q.; Wang, X.-S. Adv. Synth. Catal. 2016, 358, 3528.
[72] Sato, K.; Omote, M.; Ando, A.; Kumadaki, I. Org. Lett. 2004, 6, 4359.
[73] Sato, K.; Yuki, T.; Tarui, A.; Omote, M.; Kumadaki, I.; Ando, A. Tetrahedron Lett. 2008, 49, 3558.
[74] Yuan, W.-M.; Eriksson, L.; Szabó, K. J. Angew. Chem., Int. Ed. 2016, 55, 8410.
[75] Liu, Y.-F.; Shao, X.-X.; Zhang, P.-P.; Lu, L.; Shen, Q.-L. Org. Lett. 2015, 17, 2752.
[76] Zhang, H.-Y.; Ge, C.; Zhao, J.-Q.; Zhang, Y.-C. Org. Lett. 2017, 19, 5260.
[77] Hossain, M. J.; Ono, T.; Wakiya, K.; Hisaeda, Y. Chem. Commun. 2017, 53, 10878.
[78] Weng, Z.-Q.; Lee, R.; Jia, W.-G.; Yuan, Y.-F.; Wang, W.-F.; Feng, X.; Huang, K.-W. Organometallics 2011, 30, 3229.
[79] Xu, J.; Xiao, B.; Xie, C.-Q, Luo, D.-F.; Liu, L.; Fu, Y. Angew. Chem., Int. Ed. 2012, 51, 12551.
[80] Yin, J.; Li, Y.-M.; Zhang, R.; Jin, K.; Duan, C.-Y. Synthesis 2014, 46, 607.

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