Development of (Trifluoromethyl)zinc Reagent as Trifluoromethyl Anion and Difluorocarbene Sources

Organic Letters

Volumn 17, Issue 20, 2015, Pages 4996-4999

  Aikawa, Kohsuke ^a   Toya, Wataru ^a   Nakamura, Yuzo ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84944937842     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.5b02439     Document Type: Article

References (59)

1. Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology; Wiley-Blackwell: Chichester, U.K., 2009.
2. Petrov, V. A. Fluorinated Heterocyclic Compounds: Synthesis Chemistry and Applications; Wiley: Hoboken, 2009.
3. Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, 2 nd, completely revised and enlarged ed.; Wiley-VCH: Weinheim, 2013.
4. Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455 10.1021/cr100166a
5. Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214 10.1002/anie.201206566
6. Egami, H.; Sodeoka, M. Angew. Chem., Int. Ed. 2014, 53, 8294 10.1002/anie.201309260
7. Charpentier, J.; Früh, N.; Togni, A. Chem. Rev. 2015, 115, 650 10.1021/cr500223h
8. Xu, X.-H.; Matsuzaki, K.; Shibata, N. Chem. Rev. 2015, 115, 731 10.1021/cr500193b
9. Ni, C.; Hu, M.; Hu, J. Chem. Rev. 2015, 115, 765 10.1021/cr5002386
10. Yang, X.; Wu, T.; Phipps, R. J.; Toste, F. D. Chem. Rev. 2015, 115, 826 10.1021/cr500277b
11. Mikami, K.; Itoh, Y.; Yamanaka, M. Chem. Rev. 2004, 104, 1 10.1021/cr030685w
12. Burton, D. J.; Yang, Z.-Y. Tetrahedron 1992, 48, 189 10.1016/S0040-4020(01)88139-4
13. McClinton, M. A.; McClinton, D. A. Tetrahedron 1992, 48, 6555 10.1016/S0040-4020(01)80011-9
14. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475 10.1021/cr1004293
15. Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757 10.1021/cr9408991
16. Prakash, G. K. S.; Mandal, M. J. Fluorine Chem. 2001, 112, 123 10.1016/S0022-1139(01)00477-8
17. Shibata, N.; Mizuta, S.; Kawai, H. Tetrahedron: Asymmetry 2008, 19, 2633 10.1016/j.tetasy.2008.11.011
18. Liu, X.; Xu, C.; Wang, M.; Liu, Q. Chem. Rev. 2015, 115, 683 10.1021/cr400473a
19. Kitazume, T.; Ishikawa, N. Chem. Lett. 1982, 137 10.1246/cl.1982.137
20. Kitazume, T.; Ishikawa, N. J. Am. Chem. Soc. 1985, 107, 5186 10.1021/ja00304a026
21. Popov, I.; Lindeman, S.; Daugulis, O. J. Am. Chem. Soc. 2011, 133, 9286 10.1021/ja2041942
22. Naumann, D.; Tyrra, W.; Kock, B.; Rudolph, W.; Wilkes, B. J. Fluorine Chem. 1994, 67, 91 10.1016/0022-1139(93)02937-A
23. Tyrra, W.; Naumann, D.; Pasenok, S. V.; Yagupolskii, Y. L. J. Fluorine Chem. 1995, 70, 181 10.1016/0022-1139(94)03114-F
24. Kremlev, M. M.; Tyrra, W.; Mushta, A. I.; Naumann, D.; Yagupolskii, Y. L. J. Fluorine Chem. 2010, 131, 212 10.1016/j.jfluchem.2009.10.011
25. Aikawa, K.; Nakamura, Y.; Yokota, Y.; Toya, W.; Mikami, K. Chem.-Eur. J. 2015, 21, 96 10.1002/chem.201405677
26. Mikami, K.; Nakamura, Y.; Aikawa, K. Japanese Patent Application No. 2012-113898, filed May 18, 2012.
27. Mikami, K.; Nakamura, Y.; Negishi, K.; Aikawa, K. Japanese Patent Application No. 2013-180007, filed August 30, 2013.
28. Nakamura, Y.; Fujiu, M.; Murase, T.; Itoh, Y.; Serizawa, H.; Aikawa, K.; Mikami, K. Beilstein J. Org. Chem. 2013, 9, 2404 10.3762/bjoc.9.277
29. Lange, H.; Naumann, D. J. Fluorine Chem. 1984, 26, 435 10.1016/S0022-1139(00)80970-7
30. Schorn, C.; Naumann, D.; Scherer, H.; Hahn, J. J. Fluorine Chem. 2001, 107, 159 10.1016/S0022-1139(00)00389-4
31. Kaplan, P. T.; Xu, L.; Chen, B.; McGarry, K. R.; Yu, S.; Wang, H.; Vicic, D. A. Organometallics 2013, 32, 7552 10.1021/om401016k
32. Kaplan, P. T.; Chen, B.; Vicic, D. A. J. Fluorine Chem. 2014, 168, 158 10.1016/j.jfluchem.2014.09.023
33. Kato, H.; Hirano, K.; Kurauchi, D.; Toriumi, N.; Uchiyama, M. Chem.-Eur. J. 2015, 21, 3895 10.1002/chem.201406292
34. Wang, X.; Hirano, K.; Kurauchi, D.; Kato, H.; Toriumi, N.; Takita, R.; Uchiyama, M. Chem.-Eur. J. 2015, 21, 10993 10.1002/chem.201501811
35. Prakash, G. K. S.; Panja, C.; Vaghoo, H.; Surampudi, V.; Kultyshev, R.; Mandal, M.; Rasul, G.; Mathew, T.; Olah, G. A. J. Org. Chem. 2006, 71, 6806 10.1021/jo060835d
36. Mizuta, S.; Shibata, N.; Hibino, M.; Nagano, S.; Nakamura, S.; Toru, T. Tetrahedron 2007, 63, 8521 10.1016/j.tet.2007.05.024
37. Mizuta, S.; Shibata, N.; Akiti, S.; Fujimoto, H.; Nakamura, S.; Toru, T. Org. Lett. 2007, 9, 3707 10.1021/ol701791r
38. Nagao, H.; Yamane, Y.; Mukaiyama, T. Chem. Lett. 2007, 36, 666 10.1246/cl.2007.666
39. Zhao, H.; Qin, B.; Liu, X.; Feng, X. Tetrahedron 2007, 63, 6822 10.1016/j.tet.2007.04.068
40. Kawai, H.; Mizuta, S.; Tokunaga, E.; Shibata, N. J. Fluorine Chem. 2013, 152, 46 10.1016/j.jfluchem.2013.01.032
41. Sanhueza, I. A.; Bonney, K. J.; Nielsen, M. C.; Schoenebeck, F. J. Org. Chem. 2013, 78, 7749 10.1021/jo401099e
42. Burton, D. J.; Yang, Z.-Y.; Qiu, W. Chem. Rev. 1996, 96, 1641 10.1021/cr941140s
43. Ni, C.; Hu, J. Synthesis 2014, 46, 842 10.1055/s-0033-1340856
44. Zheng, J.; Cai, J.; Lin, J.-H.; Guo, Y.; Xiao, J.-C. Chem. Commun. 2013, 49, 7513 10.1039/c3cc44271c
45. Zheng, J.; Lin, J.-H.; Cai, J.; Xiao, J.-C. Chem.-Eur. J. 2013, 19, 15261 10.1002/chem.201303248
46. Wang, F.; Li, L.; Ni, C.; Hu, J. Beilstein J. Org. Chem. 2014, 10, 344 10.3762/bjoc.10.32
47. Li, Q.; Lin, J.-H.; Deng, Z.-Y.; Zheng, J.; Cai, J.; Xiao, J.-C. J. Fluorine Chem. 2014, 163, 38 10.1016/j.jfluchem.2014.04.011
48. Dolbier, W. R., Jr.; Battiste, M. A. Chem. Rev. 2003, 103, 1071 10.1021/cr010023b
49. Fedoryński, M. Chem. Rev. 2003, 103, 1099 10.1021/cr0100087
50. Oshiro, K.; Morimoto, Y.; Amii, H. Synthesis 2010, 2010, 2080 10.1055/s-0029-1218754
51. Wang, F.; Luo, T.; Hu, J.; Wang, Y.; Krishnan, H. S.; Jog, P. V.; Ganesh, S. K.; Prakash, G. K. S.; Olah, G. A. Angew. Chem., Int. Ed. 2011, 50, 7153 10.1002/anie.201101691
52. Wang, F.; Zhang, W.; Zhu, J.; Li, H.; Huang, K.-W.; Hu, J. Chem. Commun. 2011, 47, 2411 10.1039/C0CC04548A
53. Eusterwiemann, S.; Martinez, H.; Dolbier, W. R., Jr. J. Org. Chem. 2012, 77, 5461 10.1021/jo300876z
54. Li, L.; Wang, F.; Ni, C.; Hu, J. Angew. Chem., Int. Ed. 2013, 52, 12390 10.1002/anie.201306703
55. Gill, D. M.; McLay, N.; Waring, M. J.; Wilkinson, C. T.; Sweeney, L. B. Synlett 2014, 25, 1756 10.1055/s-0033-1341155
56. Deng, X.-Y.; Lin, J.-H.; Zheng, J.; Xiao, J.-C. Chem. Commun. 2015, 51, 8805 10.1039/C5CC02736E
57. Folléas, B.; Marek, I.; Normant, J.-F.; Saint-Jalmes, L. Tetrahedron Lett. 1998, 39, 2973 10.1016/S0040-4039(98)00391-8
58. Folléas, B.; Marek, I.; Normant, J.-F.; Saint-Jalmes, L. Tetrahedron 2000, 56, 275 10.1016/S0040-4020(99)00951-5
59. Langlois, B. R.; Billard, T. Synthesis 2003, 2, 185 10.1055/s-2003-36812