Recent Advances in Transition Metal-Promoted Trifluoromethylation Reactions

doi:10.6023/cjoc201803045

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (10): 2571-2589.DOI: 10.6023/cjoc201803045 Previous Articles Next Articles

Special Issue: 元素有机化学合辑2018-2019

Reviews

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

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 发布日期:2018-06-06
通讯作者: 杨定乔,E-mail:yangdq@scnu.edu.cn E-mail:yangdq@scnu.edu.cn
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.

Recent Advances in Transition Metal-Promoted Trifluoromethylation Reactions

Chen Donghan, Yang Wen, Yao Yongqi, Yang Xin, Deng Yingying, Yang Dingqiao

Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou 510006

Received:2018-03-27 Revised:2018-05-15 Published:2018-06-06
Contact: 10.6023/cjoc201803045 E-mail:yangdq@scnu.edu.cn
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).

Cite this article

Chen Donghan, Yang Wen, Yao Yongqi, Yang Xin, Deng Yingying, Yang Dingqiao. Recent Advances in Transition Metal-Promoted Trifluoromethylation Reactions[J]. Chin. J. Org. Chem., 2018, 38(10): 2571-2589.

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[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.

过渡金属促进三氟甲基化反应的研究进展

Recent Advances in Transition Metal-Promoted Trifluoromethylation Reactions

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