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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 8: 2322 - 2337

DOI: https://doi.org/10.6023/cjoc202003055

Recent Progress in Monofluoromethylation

  • Liu Yingjie ,
  • Li Chen ,
  • Meng Jianping ,
  • Song Dongxue ,
  • Liu Bing ,
  • Xu Ying
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  • School of Pharmacy, Harbin University of Commerce, Harbin 150076

Received date: 2020-03-24

  Revised date: 2020-04-25

  Online published: 2020-05-15

Supported by

Project supported by the Outstanding Youth Project of Natural Science Foundation of Heilongjiang Province (No. YQ2019B004) and the Youth Innovation Talent Project of Harbin University of Commerce (No. 2016QN056) and the Youth Reserve Talent Program of Harbin University of Commerce (No. 2019CX36).

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Abstract

Organic fluorides play an indispensable role in medicine, agricultural chemistry and other fields, among them fluoromethyl functional groups have strong lipophilicity, which can greatly improve the pharmacokinetics properties of drug molecules. Therefore, it is of great value to develop various fluorination reactions, especially to introduce monofluoromethyl into molecules in fluorination chemistry. The research progress of the monofluoromethylation of different structural molecules is summarized according to the classification of fluoromethyl reagents, and the possible mechanism of some reactions is discussed.

Key words： organic fluoride; fluoromethyl functional group; fluoromethyl reagent; monofluoromethylation reaction

Cite this article

Liu Yingjie , Li Chen , Meng Jianping , Song Dongxue , Liu Bing , Xu Ying . Recent Progress in Monofluoromethylation[J]. Chinese Journal of Organic Chemistry, 2020 , 40(8) : 2322 -2337 . DOI: 10.6023/cjoc202003055

References

[1] Harpere, D. B.; O'Hagan, D. Nat. Prod. Rep. 1994, 11, 123.
[2] (a) Ni, C.; Hu, M.; Hu, J. Chem. Rev. 2015, 115, 765.
(b) Xu, X.-H.; Matsuzaki, K.; Shibata, N. Chem. Rev. 2015, 115, 731.
(c) Boiko, V. N. Beilstein J. Org. Chem. 2010, 6, 880.
[3] (a) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
(b) Jeschke, P. ChemBioChem 2004, 5, 590.
[4] (a) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
(b) Wang, J.; Sánchez-Roselló, M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
(c) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315.
[5] Some examples:(a) Wang, J.; Sánchez-Roselló, M.; Aceña, J.; del Pozo, C. L.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
(b) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
(c) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
[6] (a) Wong, D. T.; Perry, K. W.; Bymaster, F. P. Nat. Rev. 2005, 4, 764.
(b) Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305.
(c) Wang, J.; Sanchez-Rosello, M.; Acena, J.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432.
[7] Some examples:(a) Kollonitsch, J.; Patchett, A. A.; Marburg, S.; Maycock, A. L.; Perkins, L. M.; Doldouras, G. A.; Duggan, D. E.; Aster, S. D. Nature 1978, 274, 906.
(b) Mckeage, K.; Keam, S. J. Drugs 2009, 69, 1799.
(c) Rojas, R. A.; Paluga, I.; Goldfrad, C. H.; Duggan, M. T.; Barnes, N. J. Asthma 2007, 44, 437.
[8] For selected examples, see:(a) Liu, X.; Xu, C.; Wang, M.; Liu, Q. Chem. Rev. 2015, 115, 683.
(b) Charpentier, J.; Fruh, N.; Togni, A. Chem. Rev. 2015, 115, 650.
(c) Chu, L.; Qing, F.-L. Acc. Chem. Res. 2014, 47, 1513.
(d) Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214.
[9] For selected examples, see:(a) Ni, C.; Hu, M.; Hu, J. Chem. Rev. 2015, 115, 765.
(b) Ni, C.; Zhu, L.; Hu, J. Acta Chim. Sinica 2015, 73, 90(in Chinese). (倪传法, 朱林桂, 胡金波, 化学学报, 2015, 73, 90.)
[10] Li, Y.; Ni, C.; Liu, J.; Zhang, L.; Zheng, J.; Zhu, L.; Hu, J. Org. Lett. 2006, 8, 1693.
[11] Ni, C.; Li, Y.; Hu, J. J. Org. Chem. 2006, 71, 6829.
[12] Liu, J.; Li, Y.; Hu, J. J. Org. Chem. 2007, 72, 3119.
[13] Liu, J.; Zhang, L.; Hu, J. Org. Lett. 2008, 10, 5377.
[14] Ni, C.; Zhang, L.; Hu, J. J. Org. Chem. 2009, 74, 3767.
[15] Fukuzumi, T.; Shibata, N.; Sugiura, M.; Yasui, H.; Nakamura, S.; Toru, T. Angew. Chem., Int. Ed. 2006, 45, 4973.
[16] Mizuta, S.; Shibata, N.; Goto, Y.; Furukawa, T.; Nakamura, S.; Toru, T. J. Am. Chem. Soc. 2007, 129, 6394.
[17] Prakash, G. K. S.; Chacko, S.; Alconcel, S.; Stewart, T.; Mathew, T.; Olah, G. A. Angew. Chem., Int. Ed. 2007, 46, 4933.
[18] Prakash, G. K. S.; Chacko, S.; Vaghoo, H.; Shao, N.; Gurung, L.; Mathew, T.; Olah, G. A. Org. Lett. 2009, 11, 1127.
[19] Ni, C.; Hu, J.; Tetrahedron Lett. 2009, 50, 7252.
[20] Furukawa, T.; Kawazoe, J.; Zhang, W.; Nishimine, T.; Tokunaga, E.; Matsumoto, T.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2011, 50, 9684.
[21] Matsuzaki, K.; Furukawa, T.; Tokunaga, E.; Matsumoto, T.; Shiro, M.; Shibata, N. Org. Lett. 2013, 15, 3282.
[22] Zhu, L.; Ni, C.; Zhao, Y.; Hu, J. Tetrahedron 2010, 66, 5089.
[23] Furukawa, T.; Goto, Y.; Kawazoe, J.; Tokunaga, E.; Nakamura, S.; Yang, Y.; Du, H.; Kakehi, A.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2010, 49, 1642.
[24] Zhao, Y.; Gao, B.; Ni, C.; Hu, J. Org. Lett. 2012, 14, 6080.
[25] Zhao, Y.; Ni, C.; Jiang, F.; Gao, B.; Shen, X.; Hu, J. ACS Catal. 2013, 3, 631.
[26] Geng, Y.; Liang, A. P.; Gao, X. Y.; Niu, C. S.; Li, J. Y.; Zou, D. P.; Wu, Y. S.; Wu, Y. J. J. Org. Chem. 2017, 82, 8604.
[27] Parisi, G.; Colella, M.; Monticelli, S.; Romanazzi, G.; Holzer, W.; Langer, T.; Degennaro, L.; Pace, V.; Luisi, R. J. Am. Chem. Soc. 2017, 139, 13648.
[28] 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. Nature 2012, 492, 95.
[29] Tang, X.; Thomoson, C. S.; Dolbier Jr., W. R. Org. Lett. 2014, 16, 4594.
[30] Tang, X.; Thomoson, C. S.; Dolbier Jr., W. R. Angew. Chem., Int. Ed. 2015, 54, 4246.
[31] He, Z.; Tan, P.; Ni, C.; Hu, J. Org. Lett. 2015, 17, 1838.
[32] Fu, W.-J.; Sun, Y.-N.; Li, X.-Y. Synth. Commun. 2019, 169, 7452.
[33] (a) Li, Y.; Lu, Y.; Qiu, G.; Ding, Q. Org. Lett. 2014, 16, 4240.
(b) Moskvina, V. S.; Khily, V. P. Chem. Heterocycl. Comp. 2019, 55, 300.
(c) Zhang, X.; Li, Y.; Hao, X.; Jin, K.; Zhang, R.; Duan, C. Tetrahedron 2018, 74, 7358.
(d) Chen, L.; Wu, L.; Duan, W.; Wang, T.; Li, L.; Zhang, K.; Zhu, J.; Peng, Z.; Xiong, F. J. Org. Chem. 2018, 83, 8607.
(e) Bu, M.-J.; Lu, G.-P.; Cai, C. Catal. Commun. 2018, 114, 70.
(f) Ni, S.-Y.; Zhou, J.; Mei, H.-B.; Han, J.-L. Tetrahedron Lett. 2018, 59, 1309.
[34] (a) Deng, X.; Chao, H.; Chen, C.; Zhou, H.; Yu, L. Sci. Bull. 2019, 64, 1280.
(b) Yu, L.; Huang, X. Synlett 2006, 2136.
(c) Yu, L.; Huang, X. Synlett 2007, 1371.
(d) Liu, M.; Li, Y.; Yu, L.; Xu, Q.; Jiang, X. Sci. China:Chem. 2018, 61, 294.
[35] Zessin, J.; Eskola, O.; Brust, P.; Bergman, J.; Steinbach, J.; Lehikoinen, P.; Solin, O.; Johannsen, B. Nucl. Med. Biol. 2001, 28, 857.
[36] Zhang, M. R.; Maeda, J.; Furutsuka, K.; Yoshida, Y.; Ogawa, M.; Suhara, T.; Suzuki, K. Bioorg. Med. Chem. Lett. 2003, 13, 201.
[37] Zhang, M. R.; Ogawa, M.; Furutsuka, K.; Yoshida, Y.; Suzuki, K. J. Fluorine Chem. 2004, 125, 1879.
[38] Zhang, W.; Zhu, L.; Hu, J. Tetrahedron 2007, 63, 10569.
[39] Doi, H.; Ban, I.; Nonoyama, A.; Sumi, K.; Kuang, C.; Hosoya, T.; Tsukada, H.; Suzuki, M. Chem.-Eur. J. 2009, 15, 4165.
[40] Hu, B.; Gao, L.; Li, C.; Hu, J. Org. Lett. 2015, 17, 3086.
[41] An, L.; Xiao, Y.-L.; Min, Q.-Q.; Zhang, X. Angew. Chem., Int. Ed. 2015, 54, 9079.
[42] Yin, H.; Sheng, J.; Zhang, K.-F.; Zhang, Z.-Q.; Bian, K.-J.; Wang, X.-S. Chem. Commun. 2019, 55, 7635.
[43] (a) Doi, H.; Ban, I.; Nonoyama, A; Sumi, K.; Kuang, C.; Hosoya, T.; Tsukada, H.; Suzuki, M. J. Chem.-Eur. 2009, 15, 4165.
(b) Hu, J.; Gao, B.; Li, L.; Ni, C. Org. Lett. 2015, 17, 3086.
(c) An, L.; Xiao, Y.-L.; Zhang, X. Angew. Chem., Int. Ed. 2015, 54, 9079.
[44] (a) Collins, B. S. L.; Wilson, C. M.; Myers, E. L.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2017, 56, 11700.
(b) Cuenca, A. B.; Shishido, R.; Ito, H.; Fernández, E. Chem. Soc. Rev. 2017, 46, 415.
(c) Fyfe, J. W. B.; Watson, A. J. B. New Tricks. Chem. 2017, 3, 31.
(d) Hemming, D.; Fritzemeier, R.; Westcott, S. A.; Santos, W. L.; Steel, P. G. Chem. Soc. Rev. 2018, 47, 7477.
[45] Wu, N.-Y.; Xu, X.-H.; Qing, F. L. ACS Catal. 2019, 9, 5726.
[46] Cao, Y.; Jiang, L.; Yi, W. Adv. Synth. Catal. 2019, 361, 4360.
[47] Ding, T.; Jiang, L.; Yang, J.; Xu, Y.; Wang, G.; Yi, W. Org. Lett. 2019, 21, 6025.
[48] Olah, G. A.; Pavlath, A. Acta Chim. Acad. Sci. Hung. 1953, 3, 425.
[49] Prakash, G. K. S.; Ledneczki, I.; Chacko, S.; Olah, G. A. Org. Lett. 2008, 10, 557.
[50] Veliks, J.; Kazia, A. Chem.-Eur. J. 2019, 25, 3786.
[51] Meanwell, N. A. J. Med. Chem. 2018, 61, 5822.
[52] Melngaile, R.; Sperga, A.; Baldridge, K. K.; Veliks, J. Org. Lett. 2019, 21, 7174.
[53] For reviews, see:(a) Okamura, H.; Bolm, C. Chem. Lett. 2004, 33, 482.
(b) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341.
[54] For selected examples, see:(a) Shen, X.; Zhang, W.; Ni, C.; Gu, Y.; Hu, J. J. Am. Chem. Soc. 2012, 134, 16999.
(b) Shen, X.; Zhang, W.; Zhang, L.; Luo, T.; Wan, X.; Gu, Y.; Hu, J. Angew. Chem., Int. Ed. 2012, 51, 6966.
(c) Zhang, W.; Huang, W.; Hu, J. Angew. Chem., Int. Ed. 2009, 48, 9858.
(d) Zhang, W.; Wang, F.; Hu, J. Org. Lett. 2009, 11, 2109.
[55] Nomura, Y.; Tokunaga, E.; Shibata, N. Angew. Chem., Int. Ed. 2011, 50, 1885.
[56] Yang, Y.-D.; Lu, X.; Liu, G.; Tokunaga, E.; Tsuzuki, S.; Shibata, N. ChemistryOpen 2012, 1, 221.
[57] Shen, X.; Zhou, M.; Ni, C.; Zhang, W.; Hu, J. Chem. Sci. 2014, 5, 117.
[58] Noto, N.; Koike, T.; Akita, M. ACS Catal. 2019, 9, 4382.
[59] Liu, Y.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2017, 56, 9930.
[60] Prakash, G. K. S.; Zhao, X.; Chacko, S.; Wang, F.; Vaghoo, H.; Olah, G. A. J. Fluorine Chem. 2008, 129, 1036.
[61] Sun, X.; Yu, S. Org. Lett. 2014, 16, 2938.
[62] Su, Y.-M.; Feng, G.-S.; Wang, Z.-Y.; L, Q.; Wang, X.-S. Angew. Chem., Int. Ed. 2015, 54, 6003.
[63] Ruan, Z.; Zhang, S.-K.; Zhu, C.; Ruth, P. N.; Stalke, D.; Ackermann, L. Angew. Chem., Int. Ed. 2017, 56, 2045.
[64] Tang, W.-K.; Feng, Y.-S.; Xu, Z.-W.; Cheng, Z.-F.; Xu, J.; Dai, J.-J.; Xu, H.-J. Org. Lett. 2017, 19, 5501.
[65] Huang, H.; Jia, K.; Chen, Y. Angew. Chem., Int. Ed. 2015, 54, 1881.
[66] (a) Jadhav, S. D.; Bakshi, D.; Singh, A. J. Org. Chem. 2015, 80, 10187.
(b) Majek, M.; Jacobi von Wangelin, A. Acc. Chem. Res. 2016, 49, 2316.
(c) Meyer, A. U.; Slanina, T.; Yao, C.-J.; König, B. ACS Catal. 2016, 6, 369.
(d) Neumann, M.; Fuldner, S.; Konig, B.; Zeitler, K. Angew. Chem., Int. Ed. 2011, 50, 951.
(e) Yu, C.; Iqbal, N.; Park, S.; Cho, E. J. Chem. Commun. 2014, 50, 12884.
[67] Tang, W.-K.; Xu, Z.-W.; Xu, J.; Tang, F.; Li, X.-X.; Dai, J.-J.; Xu, H.-J.; Feng, Y.-S. Org. Lett. 2019, 21, 196.
[68] (a) Weiss, M. E.; Kreis, L. M.; Lauber, A.; Carreira, E. M. Angew. Chem. 2011, 123, 11321.
(b) Kreis, L. M.; Krautwald, S.; Pfeiffer, N.; Martin, R. E.; Carreira, E. M. Org. Lett. 2013, 15, 1634.
[69] (a) Koide, T.; Aritome, I.; Saeki, T.; Morita, Y.; Shiota, Y.; Yoshizawa, K.; Shimakoshi, H.; Hisaeda, Y. ACS Omega 2018, 3, 4027.
(b) Tada, M.; Kaneko, K. J. Org. Chem. 1995, 60, 6635.
[70] (a) Gupta, B. D.; Roy, S. Inorg. Chim. Acta 1988, 146, 209.
(b) Giese, B.; Hartung, J.; He, J.; Huter, O.; Koch, A. Angew. Chem. 1989, 101, 334.
[71] Okabe, M.; Abe, M.; Tada, M. J. Org. Chem. 1982, 47, 1775.
[72] (a) Xia, X.-D.; Ren, Y.-L.; Chen, J.-R.; Yu, X.-L.; Lu, L.-Q.; Zou, Y.-Q.; Wan, J.; Xiao, W.-J. Chem.-Asian. J. 2015, 10, 124.
(b) Hu, X.-Q.; Chen, J.-R.; Wei, Q.; Liu, F.-L.; Deng, Q.-H.; Beauche-min, A. M.; Xiao, W.-L. Angew. Chem., Int. Ed. 2014, 53, 12163.
(c)Ding, W.; Zhou, Q.-Q.; Xuan, J.; Li, T.-R.; Lu, L.-Q.; Xiao, W.-J. Tetrahedron Lett. 2014, 55, 4648.
[73] Some examples:(a) Wang, L.; Wei, X.; Jia, W.; Zhong, J.; Wu, L.-Z.; Liu, Q. Org. Lett. 2014, 16, 5842.
(b) Jung, J.; Kim, E.; You, Y.; Cho, E. J. Adv. Synth. Catal. 2014, 356, 2741.
(c) Su, Y. M.; Hou, Y.; Yin, F.; Xu, Y. M.; Li, Y.; Zheng, X.; Wang, X. S. Org. Lett. 2014, 16, 2958.
[74] Li, W.; Zhu, Y.; Duan, Y.; Zhang, M.; Zhu, C. Adv. Synth. Catal. 2015, 357, 1277.
[75] Zhao, Q.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2017, 56, 11575.
[76] Liu, F.; Jiang, L.; Qiu, H.; Yi, W. Org. Lett. 2018, 20, 6270.
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