Recent advances in research and development of fluorin and ated drugs new methods for fluorination, mono-, di- and tri-fluoromethylation

Chinese Journal of Organic Chemistry

Volumn 34, Issue 4, 2014, Pages 662-680

  Zhang, Ji ^a   Jin, Chuanfei ^a   Zhang, Yingjun ^a  

^a HEC Pharm Group   (China)

Author keywords

Difluoromethylation; Drug design; Fluorinated drugs; Fluorination; Fluorine; Monofluoromethylation; Trifluoromethylation

Indexed keywords

EID: 84900487502     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: 10.6023/cjoc201310039     Document Type: Review

References (90)

1. Wang J., Liu H. Chin. J. Org. Chem. 2011, 31, 1785 (in Chinese).
2. Wang J., Sanchez M., Acena J., Pozo C., Sorochinsky A., Fustero S., Soloshonok V., Liu H. Chem. Rev. 2014, 114, 2432.
3. Meanwell N.A. J. Med. Chem. 2011, 54, 2529.
4. Krik K.L. Org. Process Res. Dev. 2008, 12, 305.
5. Ojima I. J. Org. Chem. 2013, 78, 6358.
6. Qing F.L. Chin. J. Org. Chem. 2012, 32, 815 (in Chinese).
7. Ritter S.K. Chem. Eng. News 2012, 90, 10.
8. Thayer A.M. Chem. Eng. News 2006, 84, 15.
9. Cui J. J., Tran M., Shen H., Nambu M., Kung P.P., Pairish M., Jia L., Meng J., Funk L., Botrous I., Mc M., Grodsky N., Ryan K., Padrique E., Alton G., Timofeevski S., Yamazaki S., Li Q., Zou H., Christensen J., Mroczkowski B., Bender S., Kania R.S., Edwards M.P. J. Med. Chem. 2011, 54, 6342.
10. Li J., Cai Y., Chen W., Liu X., Lin L., Feng X. J. Org. Chem. 2012, 77, 9148.
11. Hansen K.B., Hsiao Y., Xu F., Rivera N., Clausen A., Kubryk M., Krska S., Rosnea T., Simmons B., Balsells J., Ikemoto N., Sun Y., Spindler F., Malan C., Grabowski E.J.J., Armstrong J.D. J. Am. Chem. Soc. 2009, 131, 8798.
12. Hagmann W.K. J. Med. Chem. 2008, 51, 4359.
13. Ichikawa M., Ohtsuka M., Ohki H., Ota M., Haginoya N., Itoh M., Shibata Y., Sugita K., Ishigai Y., Terayama K., Kanda A., Usui H. ACS Med. Chem. Lett. 2013, 4, 932.
14. Hull K.L., Anani W.Q., Sanford M.S. J. Am. Chem. Soc. 2006, 128, 7134.
15. Wang X., Mei T.S., Yu J.Q. J. Am. Chem. Soc. 2009, 131, 7520.
16. Chan K.S.L., Wasa M., Wang X., Yu J.Q. Angew. Chem., Int. Ed. 2011, 50, 9081.
17. Truong T., Klimovica K., Daugulis O. J. Am. Chem. Soc. 2013, 135, 9342.
18. Ye Y., Sanford M.S. J. Am. Chem. Soc. 2013, 135, 4648.
19. Fier P.S., Luo J., Hartwig J.F. J. Am. Chem. Soc. 2013, 135, 2559.
20. Furuya T., Ritter T. J. Am. Chem. Soc. 2008, 130, 10060.
21. Mazzotti A.R., Campbell M.G., Tang P., Murphy J.M., Ritter T. J. Am. Chem. Soc. 2013, 135, 14012.
22. Ye Y., Schimler S.D., Hanley P.S., Sanford M.S. J. Am. Chem. Soc. 2013, 135, 16292.
23. Cazorla C., Metay E., Andrioletti B., Lemaire M. Tetrahedron Lett. 2009, 50, 3936.
24. Furuya T., Ritter T. Org. Lett. 2009, 11, 2860.
25. Furuya T., Strom A.E., Ritter T. J. Am. Chem. Soc. 2009, 131, 1662.
26. Tang P., Furuya T., Ritter T. J. Am. Chem. Soc. 2010, 132, 12150.
27. Lee E., Hooker J.M., Ritter T. J. Am. Chem. Soc. 2012, 134, 17456.
28. Gao Z., Lim Y.H., Tredwell M., Li L., Verhoog S., Hopkinson M., Kaluza W., Collier T.L., Passchier J., Huiban M., Gouverneur V. Angew. Chem., Int. Ed. 2012, 51, 6733.
29. Fier P.S., Hartwig J.F. J. Am. Chem. Soc. 2012, 134, 10795.
30. Sun H., Dimagno S.G. Angew. Chem., Int. Ed. 2006, 45, 2720.
31. Kumai S., Seki T., Wada A. JP 04164068, 1992
32. Kumai S., Seki T., Wada A. Chem. Abstr. 1992, 117, 233865.
33. Grushin V.V., Marshall W. J. Organometallics 2008, 27, 4825.
34. Tang P., Wang W., Ritter T. J. Am. Chem. Soc. 2011, 133, 11482.
35. Wannberg J., Wallinder C., Unlusoy M., Skold C., Larhed M. J. Org. Chem. 2013, 78, 4184.
36. Fors B.P., Watson D.A., Biscoe M.R., Buchwald S.L. J. Am. Chem. Soc. 2008, 130, 13552.
37. Nemoto H., Nishiyama T., Akai S. Org. Lett. 2011, 13, 2714.
38. Adachi K., Ohira Y., Tomizawa G., Ishihara S., Oishi S. J. Fluorine Chem. 2003, 120, 173.
39. Tian T., Zhong W.H., Meng S., Meng X.B., Li Z.J. J. Org. Chem. 2013, 78, 728.
40. Ichiishi N., Canty A.J., Yates B.F., Sanford M.S. Org. Lett. 2013, 15, 5134.
41. Olberg D.E., Arukwe J.M., Grace D., Hjelstuen O.K., Solbakken M., Kindberg G.M., Cuthbertson A. J. Med. Chem. 2010, 53, 1732.
42. Hu J., Zhang W., Wang F. Chem. Commun. 2009, 45, 7465.
43. Narjes F., Koehler K.F., Koch U., Gerlach B., Colarusso S., Steinkuhler C., Brunetti M., Altamura S., De F.R., Matassa V.G. Bioorg. Med. Chem. Lett. 2002, 12, 701.
44. Chowdhury M.A., Abdellatif K.R.A., Dong Y., Das D., Suresh M.R., Knaus E.E. J. Med. Chem. 2009, 52, 1525.
45. Fujiwara Y., Dixon J.A., Rodrigue R.A., Baxter R.D., Dixon D.D., Collins M.R., Blackmond D.G., Baran P.S. J. Am. Chem. Soc. 2012, 134, 1494.
46. Fujiwara Y., Dixon J.A., Hara F., Funder E.D., Dixon D.D., Rodrigue R.A., Baxter R.D., Herle B., Sach N., Collins M.R., Ishihara Y., Baran P.S. Nature 2012, 492, 95.
47. Xia J.B., Zhu C., Chen C. J. Am. Chem. Soc. 2013, 135, 17494.
48. Fujikawa K., Fujioka Y., Kobayashi A., Amii H. Org. Lett. 2011, 13, 5560.
49. Fier P.S., Hartwig J.F. J. Am. Chem. Soc. 2012, 134, 5524.
50. Mcmurtrey K.B., Racowski J.M., Sanford M.S. Org. Lett. 2012, 14, 4094.
51. Wang X., Zhang Y., Wang J.B. Sci. Sin. Chim. 2012, 42, 1417 (in Chinese).
52. Tomashenko O.A., Grushin V.V. Chem. Rev. 2011, 111, 4475.
53. Wu X.F., Neumann H., Beller M. Chem-Asian J. 2012, 7, 1744.
54. Furuya T., Kamlet A.S., Ritter T. Nature 2011, 473, 470.
55. Liu H., Gu Z., Jiang X. Adv. Synth. Catal. 2013, 355, 617.
56. Ji Y., Brueckl T., Baxter R.D., Fujiwara Y., Seiple I.B., Su S., Blackmond D.G., Baran P.S., Baran P.S. Proceedings of the National Academy of the Sciences of the United States of America, 2011, 108, 14411.
57. Langlois B.R., Laurent E.R.N. Tetrahedron Lett. 1991, 32, 7525.
58. Langlois B.R., Laurent E.R.N. Tetrahedron Lett. 1992, 33, 1291.
59. Ye Y., Kunzi S.A., Sanford M.S. Org. Lett. 2012, 14, 4979.
60. Ye Y., Sanford M.S. J. Am. Chem. Soc. 2012, 134, 9034.
61. Novak P., Lishchynskyi A., Grushin V.V. Angew. Chem., Int. Ed. 2012, 51, 7767.
62. Dai J.J., Fang C., Xiao B., Yi J., Xu J., Liu Z.J., Lu X., Liu L., Fu Y. J. Am. Chem. Soc. 2013, 135, 8436.
63. Danoun G., Bayarmagnai B., Grunberg M.F., Gooßen L.J. Angew. Chem., Int. Ed. 2013, 52, 7972.
64. Wang X., Xu Y., Mo F., Ji G., Qiu D., Feng J., Ye Y., Zhang S., Zhang Y., Wang J. J. Am. Chem. Soc. 2013, 135, 10330.
65. Nagib D.A., MacMillan D.W.C. Nature 2011, 480, 224.
66. Chu L., Qing F.L. J. Am. Chem. Soc. 2012, 134, 1298.
67. Liu T., Shao X., Wu Y., Shen Q. Angew. Chem., Int. Ed. 2012, 51, 540.
68. 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.
69. Mu X., Chen S., Zhen X., Liu G. Chem. Eur. J. 2011, 17, 6039.
70. Fu D., Zhang J., Cao S. J. Fluorine Chem. 2013, 156, 170.
71. Zeng Y., Zhang L., Zhao Y., Ni C., Zhao J., Hu J. J. Am. Chem. Soc. 2013, 135, 2955.
72. Wang X., Truesdale L., Yu J. J. Am. Chem. Soc. 2010, 132, 3648.
73. Su D.B., Duan J.X., Chen Q.Y. Tetrahedron Lett. 1991, 32, 7689.
74. Mulder J.A., Frutos R.P., Patel N.D., Qu B., Sun X., Tampone T.G., Gao J., Sarvestani M., Eriksson M.C., Haddad N., Shen S., Song J., Senanayake C.H. Org. Process Res. Dev. 2013, 17, 940.
75. Zhang J., Morton H.E., Ji J. Tetrahedron Lett. 2006, 47, 8733.
76. Kerdesky F.A.J., Leanna M.R., Zhang J., Li W., Lallaman J.E., Ji J., Morton H.E. Org. Process Res. Dev. 2006, 10, 512.
77. Zhao Y., Zhu L., Provencal D.P., Miller T.A., Bryan C., Langston M., Shen M., Bailey D., Sha D., Palmer T., Ho T., Li M. Org. Process Res. Dev. 2012, 16, 1652.
78. Witt A., Teodorovic P., Linderberg M., Johansson P., Minidis A. Org. Process Res. Dev. 2013, 17, 672.
79. Ojima I. Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell, 2009.
80. Petrov V.A. Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications, Wiley, 2009.
81. Roesky H.W., Sharpless K.B. Efficient Preparation of Fluorine Compounds, Wiley, New Jersey, 2012.
82. Kirsch P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, 2nd, Completely Revised and Enlarged Edition, Wiley-VCH, Weinheim, 2013.
83. Liang T., Neumann C.N., Ritter T. Angew. Chem., Int. Ed. 2013, 52, 8214.
84. Studer A. Angew. Chem., Int. Ed. 2012, 51, 8950.
85. Grushin V.V. Acc. Chem. Res. 2010, 43, 160.
86. Pan F., Shi Z. Acta Chim. Sinica 2012, 70, 1679 (in Chinese).
87. He Z., Huang Y., Verpoort F. Acta Chim Sinica 2013, 71, 700 (in Chinese).
88. Yang Y., You Z., Qing F. Acta Chim. Sinica 2012, 70, 2323 (in Chinese).
89. Zhang J., Sarma K.D., Curran T.T. Synlett 2013, 0550.
90. Zhang J., Zhang Y. J. Chin. J. Org. Chem. 2013, 33, 409 (in Chinese).