Diversity-oriented approach to CF3CHF-, CF3CFBr-, CF3CF2-, (CF3)2CH-, and CF3(SCF3)CH-substituted arenes from 1-(Diazo-2,2,2-trifluoroethyl)arenes

Organic Letters

Volumn 16, Issue 22, 2014, Pages 6004-6007

  Emer, Enrico ^a   Twilton, Jack ^a   Tredwell, Matthew ^a   Calderwood, Samuel ^a   Collier, Thomas Lee ^c   Liégault, Benoît ^a,b   Taillefer, Marc ^b   Gouverneur, Véronique ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b INSTITUT CHARLES GERHARDT   (France)

^c Advion BioSciences Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZO COMPOUND; BROMINATED HYDROCARBON; FLUORINATED HYDROCARBON; FLUORINE;

CHEMICAL STRUCTURE; CHEMISTRY; POSITRON EMISSION TOMOGRAPHY; SYNTHESIS;

AZO COMPOUNDS; FLUORINE RADIOISOTOPES; HYDROCARBONS, BROMINATED; HYDROCARBONS, FLUORINATED; MOLECULAR STRUCTURE; POSITRON-EMISSION TOMOGRAPHY;

EID: 84912524115     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5030184     Document Type: Article

References (64)

1. Bégué, J.-P.; Bonnet-Delpon, D. J. Fluorine Chem. 2006, 127, 992-1012
2. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881-1886
3. OHagan, D. Chem. Soc. Rev. 2008, 37, 308-319
4. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320-330
5. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359-4369
6. Fluorine in Medicinal Chemistry and Chemical Biology; Ojima, I., Ed.; Wiley-Blackwell: New York, 2009.
7. Fluorine in Pharmaceutical and Medicinal Chemistry: From Biophysical Aspects to Clinical Applications; Gouverneur, V.; Muller, K., Eds.; Imperial College Press: London, 2012.
8. 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, 2432-2506
9. Zhu, W.; Wang, J.; Wang, S.; Gu, Z.; Aceña, J. L.; Izawa, K.; Liu, H.; Soloshonok, V. A. J. Fluorine Chem. 2014, 167, 37-54
10. Theodoridis, G. In Advances in Fluorine Science: Fluorine and the Environment-Agrochemicals, Archaeology, Green Chemistry & Water; Tressaud, A., Ed.; Elsevier: Amsterdam, 2006; Vol. 2, pp 121-175.
11. Fujiwara, T.; OHagan, D. J. Fluorine Chem. 2014, 167, 16-29
12. Furuya, T.; Klein, J. E. M. N.; Ritter, T. Synthesis 2010, 1804-1821
13. Hollingworth, C.; Gouverneur, V. Chem. Commun. 2012, 48, 2929-2942
14. Campbell, M. G.; Ritter, T. Org. Process. Rev. Dev. 2014, 18, 474-480
15. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475-4521
16. Liu, T.; Shen, Q. Eur. J. Org. Chem. 2012, 34, 6679-6687
17. Robertson, J. F. R.; Come, S. E.; Jones, S. E.; Beex, F.; Kaufmann, M.; Makris, A.; Nortier, J. W. R.; Possinger, K.; Rutqvist, L.-E. Eur. J. Cancer 2005, 41, 346-356
18. Regitz, M.; Maas, G. In Diazo Compounds: Properties and Syntheses; Academic Press: Orlando, FL, 1986.
19. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160
20. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley: Chichester, UK, 1998.
21. Davies, H. M. L.; Denton, J. R. Chem. Soc. Rev. 2009, 38, 3061-3071
22. Olah, G. A.; Welch, J. Synthesis 1974, 896-898
23. Takeuchi, Y.; Takagi, K.; Yamaba, T.; Nabetani, M.; Koizumi, Y. J. Fluorine Chem. 1994, 68, 149-154
24. Doherty, G.; Cook, A. Patent WO 2008/024746 A1, 2008.
25. Pasceri, R.; Bartrum, H. E.; Hayes, C. J.; Moody, C. J. Chem. Commun. 2012, 48, 12077-12079
26. Qin, C.; Davies, H. M. L. Org. Lett. 2013, 15, 6152-6154
27. Yadav, A. K.; Srivastava, V. P.; Yadav, L. D. S. Chem. Commun. 2013, 49, 2154-2156
28. Tao, J.; Tran, R.; Murphy, G. K. J. Am. Chem. Soc. 2013, 135, 16312-16315
29. Hu, M.; Ni, C.; Hu, J. J. Am. Chem. Soc. 2012, 134, 15257-15260
30. Wang, X.; Zhou, Y.; Ji, G.; Wu, G.; Li, M.; Zhang, Y.; Wang, J. Eur. J. Org. Chem. 2014, 3093-3096
31. Hu, M.; Rong, J.; Miao, W.; Ni, C.; Han, Y.; Hu, J. Org. Lett. 2014, 16, 2030-2033
32. Lefebvre, Q.; Fava, E.; Nikolaienko, P.; Rueping, M. Chem. Commun. 2014, 50, 6617-6619
33. For a review on trifluoromethylketones, see: Kelly, C. B.; Mercadantea, M. A.; Leadbeater, N. E. Chem. Commun. 2013, 49, 11133-11148
34. Shepard, R. A.; Wentworth, S. E. J. Org. Chem. 1967, 32, 3197-3199
35. Shi, G.; Xu, Y. J. Fluorine Chem. 1990, 46, 173-178
36. Denton, J. R.; Sukumaran, D.; Davies, H. M. L. Org. Lett. 2007, 9, 2625-2628
37. Uehara, M.; Suematsu, H.; Yasutomi, Y.; Katsuki, T. J. Am. Chem. Soc. 2011, 133, 170-171
38. Hyster, T. K.; Ruhl, K. E.; Rovis, T. J. Am. Chem. Soc. 2013, 135, 5364-5367
39. Wang, X.; Xu, Y.; Deng, Y.; Zhou, Y.; Feng, J.; Ji, G.; Zhang, Y.; Wang, J. Chem.-Eur. J. 2014, 961-965
40. Anilkumar, R.; Burton, D. J. Tetrehedron Lett. 2003, 44, 6661-6664
41. Tahara, R.; Fukuhara, T.; Hara, S. J. Fluorine Chem. 2011, 132, 579-586
42. 3 motif has been reported to date. See: Winter, R. W.; Dodean, R.; Smith, J. A.; Anilkumar, R.; Burton, D. J.; Gard, G. L. J. Fluorine Chem. 2005, 126, 1202-1214
43. Langlois, B. R.; Roques, N. J. Fluorine Chem. 2007, 128, 1318-1325
44. Büttner, S.; Lubbe, M.; Reinke, H.; Fischer, C.; Langer, P. Tetrahedron 2008, 64, 7968-7976
45. Kremlev, M. M.; Tyrra, W.; Mushta, A. I.; Naumann, D.; Yagupolskii, Y. L. J. Fluorine Chem. 2010, 131, 212-216
46. Tahara, R.; Fukuhara, T.; Hara, S. J. Fluorine Chem. 2011, 132, 579-586
47. Schareina, T.; Wu, X.-F.; Zapf, A.; Cotté, A.; Beller, M. Top. Catal. 2012, 55, 426-431
48. Serizawa, H.; Aikawa, K.; Mikami, K. Org. Lett. 2014, 16, 3456-3459
49. Litvinas, N. D.; Fier, P. S.; Harwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 536-539
50. Zatolochnaya, O. V.; Gevorgyan, V. Org. Lett. 2013, 15, 2562-2565
51. Cui, L.; Matusaki, Y.; Tada, N.; Miura, T.; Uno, B.; Itoh, A. Adv. Synth. Catal. 2013, 355, 2203-2207
52. Mormino, M. G.; Fier, P. S.; Hartwig, J. F. Org. Lett. 2014, 16, 1744-1747
53. Yoneda, N. J. Fluorine Chem. 2004, 125, 7-17
54. Arrica, M. A.; Wirth, T. Eur. J. Org. Chem. 2005, 395-400
55. Klabunde, K. J.; Burton, D. J. J. Am. Chem. Soc. 1972, 94, 820-828
56. Kawai, H.; Furukawa, T.; Nomura, Y.; Tokunaga, E.; Shibata, N. Org. Lett. 2011, 13, 3596-3599
57. Zhao, Y.; Hu, J. Angew. Chem., Int. Ed. 2012, 51, 1033-1036
58. Zhu, L.; Liu, S.; Douglas, J. T.; Altman, R. A. Chem.-Eur. J. 2013, 12800-12805
59. Song, W.; Lackner, S.; Ackermann, L. Angew. Chem., Int. Ed. 2014, 53, 2477-2480
60. Qiao, Y.; Si, T.; Yang, M.-H.; Altman, R. A. J. Org. Chem. 2014, 79, 7122-7131 and references therein
61. Huiban, M.; Tredwell, M.; Mizuta, S.; Wan, Z.; Zhang, X.; Collier, T. L.; Gouverneur, V.; Passchier, J. Nat. Chem. 2013, 5, 941-944
62. Evans, S. M.; Fraker, D.; Hahn, S. M.; Gleason, K.; W. Jenkins, W. T.; Jenkins, K.; Hwang, W.; Zhang, P.; Mick, R.; Koch, C. J. Int. J. Radiat. Oncol. Biol. Phys. 2006, 64, 922-927
63. Dolbiera, W. R., Jr.; Lia, A.; Koch, C. J.; Shiuec, C.; Kachurb, A. V. Appl. Radiat. Isot. 2001, 54, 73-80
64. Ziemer, L. S.; Evans, S. M.; Kachur, A. V.; Shuman, A. L.; Cardi, C. A.; Jenkins, W. T.; Karp, J. S.; Alavi, A.; Dolbier, W. R., Jr.; Koch, C. J. Eur. J. Nucl. Med. 2003, 30, 259-266