Nickel-Catalyzed Allylic C(sp3)-F Bond Activation of Trifluoromethyl Groups via β-Fluorine Elimination: Synthesis of Difluoro-1,4-dienes

ACS Catalysis

Volumn 5, Issue 10, 2015, Pages 5947-5950

  Ichitsuka, Tomohiro ^a   Fujita, Takeshi ^a   Ichikawa, Junji ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

1,4 dienes; alkynes; C F bond activation; nickel catalysis; trifluoromethylalkenes; fluorine elimination

Indexed keywords

CATALYSIS; CHEMICAL ACTIVATION; FLUORINE; HYDROCARBONS;

1 ,4-DIENES; ALKYNES; C-F BOND ACTIVATIONS; NICKEL CATALYSIS; TRIFLUOROMETHYLALKENES;

NICKEL;

EID: 84943190000     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/acscatal.5b01463     Document Type: Article

References (56)

1. Burdeniuc, J.; Jedicka, B.; Crabtree, R. H. Chem. Ber. 1997, 130, 145-154 10.1002/cber.19971300203
2. Amii, H.; Uneyama, K. Chem. Rev. 2009, 109, 2119-2183 10.1021/cr800388c
3. Stahl, T.; Klare, H. F. T.; Oestreich, M. ACS Catal. 2013, 3, 1578-1587 10.1021/cs4003244
4. Ahrens, T.; Kohlmann, J.; Ahrens, M.; Braun, T. Chem. Rev. 2015, 115, 931-972 10.1021/cr500257c
5. Unzner, T. A.; Magauer, T. Tetrahedron Lett. 2015, 56, 877-883 10.1016/j.tetlet.2014.12.145
6. Fuchibe, K.; Kaneko, T.; Mori, K.; Akiyama, T. Angew. Chem., Int. Ed. 2009, 48, 8070-8073 10.1002/anie.200901986
7. Terao, J.; Nakamura, M.; Kambe, N. Chem. Commun. 2009, 6011-6013 10.1039/b915620h
8. Ichikawa, J. Yuki Gosei Kagaku Kyokaishi 2010, 68, 1175-1184 10.5059/yukigoseikyokaishi.68.1175
9. Iida, T.; Hashimoto, R.; Aikawa, K.; Ito, S.; Mikami, K. Angew. Chem., Int. Ed. 2012, 51, 9535-9538 10.1002/anie.201203588
10. Fuchibe, K.; Takahashi, M.; Ichikawa, J. Angew. Chem., Int. Ed. 2012, 51, 12059-12062 10.1002/anie.201206946
11. Wu, G.; Deng, Y.; Wu, C.; Wang, X.; Zhang, Y.; Wang, J. Eur. J. Org. Chem. 2014, 2014, 4477-4481 10.1002/ejoc.201402597
12. Ichitsuka, T.; Fujita, T.; Arita, T.; Ichikawa, J. Angew. Chem., Int. Ed. 2014, 53, 7564-7568 10.1002/anie.201402695
13. Ichikawa, J.; Nadano, R.; Ito, N. Chem. Commun. 2006, 4425-4427 10.1039/b610690k
14. Miura, T.; Ito, Y.; Murakami, M. Chem. Lett. 2008, 37, 1006-1007 10.1246/cl.2008.1006
15. Corberán, R.; Mszar, N. W.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2011, 50, 7079-7082 10.1002/anie.201102398
16. Hu, M.; He, Z.; Gao, B.; Li, L.; Ni, C.; Hu, J. J. Am. Chem. Soc. 2013, 135, 17302-17305 10.1021/ja409941r
17. Zhang, Z.; Zhou, Q.; Yu, W.; Li, T.; Wu, G.; Zhang, Y.; Wang, J. Org. Lett. 2015, 17, 2474-2477 10.1021/acs.orglett.5b00980
18. Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1994, 116, 5975-5976 10.1021/ja00092a061
19. Montgomery, J.; Savchenko, A. V. J. Am. Chem. Soc. 1996, 118, 2099-2100 10.1021/ja952026+
20. Montgomery, J. Acc. Chem. Res. 2000, 33, 467-473 10.1021/ar990095d
21. Ikeda, S. Acc. Chem. Res. 2000, 33, 511-519 10.1021/ar9901016
22. Montgomery, J. Angew. Chem., Int. Ed. 2004, 43, 3890-3908 10.1002/anie.200300634
23. Moslin, R. M.; Miller-Moslin, K.; Jamison, T. F. Chem. Commun. 2007, 4441-4449 10.1039/b707737h
24. Sun, A. D.; Love, J. A. Org. Lett. 2011, 13, 2750-2753 10.1021/ol200860t
25. Tobisu, M.; Xu, T.; Shimasaki, T.; Chatani, N. J. Am. Chem. Soc. 2011, 133, 19505-19511 10.1021/ja207759e
26. Jin, Z.; Li, Y.-J.; Ma, Y.-Q.; Qiu, L.-L.; Fang, J.-X. Chem.-Eur. J. 2012, 18, 446-450 10.1002/chem.201103050
27. Fischer, P.; Götz, K.; Eichhorn, A.; Radius, U. Organometallics 2012, 31, 1374-1383 10.1021/om2009815
28. Nakamura, Y.; Yoshikai, N.; Ilies, L.; Nakamura, E. Org. Lett. 2012, 14, 3316-3319 10.1021/ol301195x
29. Dai, W.; Xiao, J.; Jin, G.; Wu, J.; Cao, S. J. Org. Chem. 2014, 79, 10537-10546 10.1021/jo5022234
30. Clot, E.; Eisenstein, O.; Jasim, N.; Macgregor, S. A.; McGrady, J. E.; Perutz, R. N. Acc. Chem. Res. 2011, 44, 333-348 10.1021/ar100136x
31. Weaver, J.; Senaweera, S. Tetrahedron 2014, 70, 7413-7428 10.1016/j.tet.2014.06.004
32. Kuhl, S.; Schneider, R.; Fort, Y. Adv. Synth. Catal. 2003, 345, 341-344 10.1002/adsc.200390036
33. Fischer, P.; Götz, K.; Eichhorn, A.; Radius, U. Organometallics 2012, 31, 1374-1383 10.1021/om2009815
34. Kuehnel, M. F.; Lentz, D.; Braun, T. Angew. Chem., Int. Ed. 2013, 52, 3328-3348 and references cited therein 10.1002/anie.201205260
35. Liu, P.; McCarren, P.; Cheong, P. H.-Y.; Jamison, T. F.; Houk, K. N. J. Am. Chem. Soc. 2010, 132, 2050-2057 10.1021/ja909562y
36. Liu, P.; Montgomery, J.; Houk, K. N. J. Am. Chem. Soc. 2011, 133, 6956-6959 10.1021/ja202007s
37. Hintermann, L.; Läng, F.; Maire, P.; Togni, A. Eur. J. Inorg. Chem. 2006, 2006, 1397-1412 10.1002/ejic.200500795
38. Narumi, T.; Tomita, K.; Inokuchi, E.; Kobayashi, K.; Oishi, S.; Ohno, H.; Fujii, N. Org. Lett. 2007, 9, 3465-3468 10.1021/ol701627v
39. Hazari, A.; Gouverneur, V.; Brown, J. M. Angew. Chem., Int. Ed. 2009, 48, 1296-1299 10.1002/anie.200804310
40. Pigeon, X.; Bergeron, M.; Barabé, F.; Dubé, P.; Frost, H. N.; Paquin, J.-F. Angew. Chem., Int. Ed. 2010, 49, 1123-1127 10.1002/anie.200904747
41. Ohashi, M.; Shibata, M.; Ogoshi, S. Angew. Chem., Int. Ed. 2014, 53, 13578-13582 10.1002/anie.201408467
42. Lappert, M. F.; Speier, G. J. Organomet. Chem. 1974, 80, 329-339 10.1016/S0022-328X(00)80011-X
43. Iluc, V. M.; Hillhouse, G. L. Tetrahedron 2006, 62, 7577-7582 10.1016/j.tet.2006.05.055
44. Zell, T.; Schaub, T.; Radacki, K.; Radius, U. Dalton Trans. 2011, 40, 1852-1854 10.1039/c0dt01442g
45. Tillack, A.; Pulst, S.; Baumann, W.; Baudisch, H.; Kortus, K.; Rosenthal, U. J. Organomet. Chem. 1997, 532, 117-123 10.1016/S0022-328X(96)06734-4
46. Chaulagain, M. R.; Mahandru, G. M.; Montgomery, J. Tetrahedron 2006, 62, 7560-7566 10.1016/j.tet.2006.03.120
47. Bobek, M.; Kavai, I.; De Clercq, E. J. Med. Chem. 1987, 30, 1494-1497 10.1021/jm00391a036
48. Moore, W. R.; Schatzman, G. L.; Jarvi, E. T.; Gross, R. S.; McCarthy, J. R. J. Am. Chem. Soc. 1992, 114, 360-361 10.1021/ja00027a056
49. Magueur, G.; Crousse, B.; Ourévitch, M.; Bonnet-Delpon, D.; Bégué, J.-P. J. Fluorine Chem. 2006, 127, 637-642 10.1016/j.jfluchem.2005.12.013
50. Amii, H.; Kobayashi, T.; Hatamoto, Y.; Uneyama, K. Chem. Commun. 1999, 1323-1324 10.1039/a903681d
51. Ichikawa, J. Pure Appl. Chem. 2000, 72, 1685-1689 10.1351/pac200072091685
52. Qiu, X.-L.; Qing, F.-L. J. Org. Chem. 2002, 67, 7162-7164 10.1021/jo0257400
53. Ichikawa, J.; Wada, Y.; Fujiwara, M.; Sakoda, K. Synthesis 2002, 2002, 1917-1936 10.1055/s-2002-33912
54. Ichikawa, J. Chim. Oggi 2007, 25 (4) 54-57
55. Gao, B.; Zhao, Y.; Hu, J. Angew. Chem., Int. Ed. 2015, 54, 638-642 10.1002/anie.201409705
56. Fuchibe, K.; Morikawa, T.; Shigeno, K.; Fujita, T.; Ichikawa, J. Org. Lett. 2015, 17, 1126-1129 10.1021/ol503759d