C-H Difluoroalkylation of Aldehyde Hydrazones with Functionalized Difluoromethyl Bromides under Copper Catalysis

ACS Catalysis

Volumn 6, Issue 2, 2016, Pages 1093-1096

  Prieto, Alexis ^a   Melot, Romain ^a   Bouyssi, Didier ^a   Monteiro, Nuno ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

copper; difluoromethylation; halides; hydrazones; synthetic methods

Indexed keywords

ALDEHYDES; COPPER;

COPPER CATALYSIS; DIFLUOROMETHYLATION; FUNCTIONALIZED; HALIDES; HYDRAZONES; REACTION YIELDS; SYNTHETIC METHODS;

CATALYSIS;

EID: 84957592004     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/acscatal.5b02755     Document Type: Article

References (50)

1. Fluorine in Medicinal Chemistry and Chemical Biology; Ojima, I., Ed., Wiley: Chichester, 2009.
2. O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308-319 10.1039/B711844A
3. Purser, S. P.; Moore, R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320-330 10.1039/B610213C
4. Hagmann, W. K. J. Med. Chem. 2008, 51, 4359-4369 10.1021/jm800219f
5. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881-1886 10.1126/science.1131943
6. Meanwell, N. A. J. Med. Chem. 2011, 54, 2529-2591 10.1021/jm1013693
7. Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470-477 10.1038/nature10108
8. Tomashenko, O. A.; Grushin, V. V. Chem. Rev. 2011, 111, 4475-4521 10.1021/cr1004293
9. Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8950-8958 10.1002/anie.201202624
10. Besset, T.; Schneider, C.; Cahard, D. Angew. Chem., Int. Ed. 2012, 51, 5048-5050 10.1002/anie.201201012
11. Jin, Z.; Hammond, G. B.; Xu, B. Aldrichimica Acta 2012, 45, 67-83
12. Landelle, G.; Panossian, A.; Pazenok, S.; Vors, J.-P.; Leroux, F. R. Beilstein J. Org. Chem. 2013, 9, 2476-2536 10.3762/bjoc.9.287
13. Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214-8264 10.1002/anie.201206566
14. Liu, H.; Gu, Z.; Jiang, X. Adv. Synth. Catal. 2013, 355, 617-626 10.1002/adsc.201200764
15. Chen, B.; Vicic, D. A. Top. Organomet. Chem. 2014, 52, 113-141 10.1007/3418-2014-87
16. Prieto, A.; Baudoin, O.; Bouyssi, D.; Monteiro, N. Chem. Commun. 2016, 52, 869-881 10.1039/C5CC05954B
17. For an excellent, exhaustive review of transition metal-catalyzed difluoroalkylation processes, see: Belhomme, M.-C.; Besset, T.; Poisson, T.; Pannecoucke, X. Chem.-Eur. J. 2015, 21, 12836-12865 10.1002/chem.201501475
18. Lazny, R.; Nodzewska, A. Chem. Rev. 2010, 110, 1386-1434 10.1021/cr900067y
19. Brehme, R.; Enders, D.; Fernandez, R.; Lassaletta, J. M. Eur. J. Org. Chem. 2007, 2007, 5629-5660 10.1002/ejoc.200700746
20. Prieto, A.; Melot, R.; Bouyssi, D.; Monteiro, N. Angew. Chem., Int. Ed. 2016, 55, DOI: 10.1002/anie.201510334.
21. Pair, E.; Monteiro, N.; Bouyssi, D.; Baudoin, O. Angew. Chem., Int. Ed. 2013, 52, 5346-5349 10.1002/anie.201300782
22. Prieto, A.; Jeamet, E.; Monteiro, N.; Bouyssi, D.; Baudoin, O. Org. Lett. 2014, 16, 4770-4773 10.1021/ol5022228
23. Prieto, A.; Landart, M.; Baudoin, O.; Monteiro, N.; Bouyssi, D. Adv. Synth. Catal. 2015, 357, 2939-2943 10.1002/adsc.201500237
24. Belhomme, M.-C.; Poisson, T.; Pannecoucke, X. Org. Lett. 2013, 15, 3428-3431 10.1021/ol401483j
25. Belhomme, M.-C.; Poisson, T.; Pannecoucke, X. J. Org. Chem. 2014, 79, 7205-7211 10.1021/jo5010907
26. Caillot, G.; Dufour, J.; Belhomme, M.-C.; Poisson, T.; Grimaud, L.; Pannecoucke, X.; Gillaizeau, I. Chem. Commun. 2014, 50, 5887-5890 10.1039/c4cc01994f
27. Belhomme, M.-C.; Dru, D.; Xiong, H.-Y.; Cahard, D.; Besset, T.; Poisson, T.; Pannecoucke, X. Synthesis 2014, 46, 1859-1870 10.1055/s-0033-1338637
28. Belhomme, M.-C.; Bayle, A.; Poisson, T.; Pannecoucke, X. Eur. J. Org. Chem. 2015, 2015, 1719-1726 10.1002/ejoc.201403656
29. For a previous synthesis of 4,4-difluoropyrazol-5-ones, see: Surmont, R.; Verniest, G.; De Kimpe, N. Org. Lett. 2010, 12, 4648-4651 10.1021/ol1019713
30. Ma, G.; Wan, W.; Li, J.; Hu, Q.; Jiang, H.; Zhu, S.; Wang, J.; Hao, J. Chem. Commun. 2014, 50, 9749-9752 10.1039/C4CC04591B
31. Egami, H.; Ide, T.; Kawato, Y.; Hamashima, Y. Chem. Commun. 2015, 51, 16675-16678 10.1039/C5CC07011B
32. Kawamura, S.; Egami, H.; Sodeoka, M. J. Am. Chem. Soc. 2015, 137, 4865-4873 10.1021/jacs.5b02046
33. Stanek, K.; Koller, R.; Togni, A. J. Org. Chem. 2008, 73, 7678-7685 10.1021/jo8014825
34. Baldwin, J. E. Chem. Rev. 2003, 103, 1197-1212 10.1021/cr010020z
35. Zhang, F.; Min, Q.-Q.; Zhang, X. Synthesis 2015, 47, 2912-2923 10.1055/s-0035-1560457
36. Yang, Z.-Y.; Burton, D. J. J. Fluorine Chem. 1989, 45, 435-439 10.1016/S0022-1139(00)82877-8
37. Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1991, 56, 5125-5132 10.1021/jo00017a026
38. Kitagawa, O.; Miura, A.; Kobayashi, Y.; Taguchi, T. Chem. Lett. 1990, 1011-1014 10.1246/cl.1990.1011
39. Sato, K.; Omote, M.; Ando, A.; Kumadaki, I. J. Fluorine Chem. 2004, 125, 509-515 10.1016/j.jfluchem.2003.11.023
40. Ponomarenko, M. V.; Serguchev, Y. A.; Ponomarenko, B. V.; Röschenthaler, G.-V.; Fokin, A. A. J. Fluorine Chem. 2006, 127, 842-849 10.1016/j.jfluchem.2006.03.006
41. Burton, D. J.; Kehoe, L. J. J. Org. Chem. 1970, 35, 1339-1342 10.1021/jo00830a018
42. Burton, D. J.; Kehoe, L. J. J. Org. Chem. 1971, 36, 2596-2599 10.1021/jo00817a006
43. Mitani, M.; Masuda, M.; Inoue, A. Synlett 2004, 1227-1230 10.1055/s-2004-825579
44. Nenajdenko, V. G.; Muzalevskiy, V. M.; Shastin, A. V. Chem. Rev. 2015, 115, 973-1050 10.1021/cr500465n
45. Miyabe, H.; Yoshioda, E.; Kohtani, S. Curr. Org. Chem. 2010, 14, 1254-1264 10.2174/138527210791330477
46. Friestad, G. K. Eur. J. Org. Chem. 2005, 2005, 3157-3172 10.1002/ejoc.200500232
47. Miyabe, H.; Ueda, M.; Naito, T. Synlett 2004, 1140-1157 10.1055/s-2004-822889
48. Friestad, G. K. Tetrahedron 2001, 57, 5461-5496 10.1016/S0040-4020(01)00384-2
49. Fallis, A. G.; Brinza, I. M. Tetrahedron 1997, 53, 17543-17594 10.1016/S0040-4020(97)10060-6
50. At the time of submission of the present manuscript, a paper by Li and Zhu appeared in the literature reporting the iridium-photocatalyzed difluoroalkylation of hydrazones. Notably, the synthetic utility of the difluoroalkylated hydrazones was further illustrated through their conversion to difluorinated hydrazines by reduction of the hydrazone moiety: Xu, P.; Wang, G.; Zhu, Y.; Li, W.; Cheng, Y.; Li, S.; Zhu, C. Angew. Chem., Int. Ed. 2016, 55, DOI: 10.1002/anie.201508698.