A facile parallel synthesis of trifluoroethyl-substituted alkynes

Angewandte Chemie - International Edition

Volumn 51, Issue 25, 2012, Pages 6227-6230

  Liu, Cui Bo ^a   Meng, Wei ^a   Li, Feng ^a   Wang, Shuai ^a   Nie, Jing ^a   Ma, Jun An ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

alkynes; cross coupling; diazo compounds; homogeneous catalysis; trifluoroethylation

Indexed keywords

ALKYNES; CROSS-COUPLINGS; DIAZO COMPOUNDS; HOMOGENEOUS CATALYSIS; TRIFLUOROETHYLATION;

REACTION KINETICS;

ACETYLENE;

ALKYNE; TRIFLUOROETHANOL;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKYNES; CATALYSIS; MOLECULAR STRUCTURE; TRIFLUOROETHANOL;

EID: 84862676151     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201202372     Document Type: Article

References (69)

1. Organofluorine Compounds: Chemistry and Applications (Ed.:, T. Hiyama,), Springer, New York, 2000
2. P. Kirsch, Modern Fluoroorganic Chemistry: Synthesis Reactivity, Applications, Wiley-VCH, Weinheim, 2004
3. M. Shimizu, T. Hiyama, Angew. Chem. 2005, 117, 218
4. Angew. Chem. Int. Ed. 2005, 44, 214
5. K. Uneyama, T. Katagiri, H. Amii, Acc. Chem. Res. 2008, 41, 817
6. S. Purser, P. R. Moore, S. Swallow, V. Gouverneur, Chem. Soc. Rev. 2008, 37, 320
7. J.-A. Ma, D. Cahard, Chem. Rev. 2008, 108, PR 1
8. N. Shibata, S. Mizuta, H. Kawai, Tetrahedron: Asymmetry 2008, 19, 2633
9. K. L. Kirk, Org. Process Res. Dev. 2008, 12, 305
10. Fluorine in Medicinal Chemistry and Chemical Biology (Ed.:, I. Ojima,), Wiley-Blackwell, Chichester, 2009
11. J. Hu, W. Zhang, F. Wang, Chem. Commun. 2009, 7465
12. S. Lectard, Y. Hamashima, M. Sodeoka, Adv. Synth. Catal. 2010, 352, 2708
13. J. Nie, H.-C. Guo, D. Cahard, J.-A. Ma, Chem. Rev. 2011, 111, 455
14. O. A. Tomashenko, V. V. Grushin, Chem. Rev. 2011, 111, 4475.
15. H. Gilman, R. G. Jones, J. Am. Chem. Soc. 1943, 65, 1458
16. R. N. Haszeldine, J. Chem. Soc. 1964, 1881
17. J. H. Atherton, R. Fields, J. Chem. Soc. C 1968, 1507
18. J. H. Atherton, R. Fields, J. Chem. Soc. C 1968, 2276
19. W. L. Mock, M. E. Hartman, J. Org. Chem. 1977, 42, 459
20. W. L. Mock, M. E. Hartman, J. Org. Chem. 1977, 42, 466
21. R. Fields, J. P. Tomlinson, J. Fluorine Chem. 1979, 14, 19
22. M. Tordeux, C. Wakselman, J. Fluorine Chem. 1981, 17, 299
23. M. Tordeux, C. Wakselman, J. Fluorine Chem. 1982, 21, 99.
24. P. Le Maux, S. Juillard, G. Simmoneaux, Synthesis 2006, 1701
25. P. K. Mykhailiuk, S. Afonin, G. V. Palamarchuk, O. V. Shishkin, A. S. Ulrich, I. V. Komarov, Synthesis 2008, 1757
26. P. K. Mykhailiuk, S. Afonin, G. V. Palamarchuk, O. V. Shishkin, A. S. Ulrich, I. V. Komarov, Angew. Chem. 2008, 120, 5849
27. Angew. Chem. Int. Ed. 2008, 47, 5765
28. O. O. Grygorenko, O. S. Artamonov, I. V. Komarov, P. K. Mykhailiuk, Tetrahedron 2011, 67, 803.
29. B. Morandi, E. M. Carreira, Angew. Chem. 2010, 122, 950
30. Angew. Chem. Int. Ed. 2010, 49, 938
31. B. Morandi, E. M. Carreira, Angew. Chem. 2010, 122, 4390
32. Angew. Chem. Int. Ed. 2010, 49, 4294
33. B. Morandi, B. Mariampillai, E. M. Carreira, Angew. Chem. 2011, 123, 1133
34. Angew. Chem. Int. Ed. 2011, 50, 1101
35. B. Morandi, E. M. Carreira, Angew. Chem. 2011, 123, 9251
36. Angew. Chem. Int. Ed. 2011, 50, 9085
37. B. Morandi, J. Cheang, E. M. Carreira, Org. Lett. 2011, 13, 3080.
38. A. Solladié-Cavallo, J. Suffert, Tetrahedron Lett. 1984, 25, 1897
39. A. Solladié-Cavallo, D. Farkhani, S. Fritz, T. Lazrak, J. Suffert, Tetrahedron Lett. 1984, 25, 4117
40. A. Solladié-Cavallo, J. Suffert, Synthesis 1985, 659
41. A. Solladié-Cavallo, D. Farkhani, A. C. Dreyfuss, F. Sanch, Bull. Soc. Chim. Fr. 1986, 6, 906
42. Z.-Y. Long, Q.-Y. Chen, Tetrahedron Lett. 1998, 39, 8487
43. G. B. Hammond, R. G. Plevey, P. Sampson, J. C. Tatlow, J. Fluorine Chem. 1988, 40, 81
44. M. R. Schneider, J. Med. Chem. 1986, 29, 1494
45. S. Matsubara, M. Mitani, K. Utimoto, Tetrahedron Lett. 1987, 28, 5857
46. D. A. Culkin, J. F. Hartwig, Organometallics 2004, 23, 3398
47. J. Balsells, M. Waters, K. Hansen, G. R. Kieczykowski, Z. J. Song, Synthesis 2007, 2779
48. K. Takai, T. Takagi, T. Baba, T. Kanamori, J. Fluorine Chem. 2007, 128, 120
49. Y. Zhao, J. Hu, Angew. Chem. 2012, 124, 1057
50. Angew. Chem. Int. Ed. 2012, 51, 1033.
51. H. Kawai, T. Furukawa, Y. Nomura, E. Tokunaga, N. Shibata, Org. Lett. 2011, 13, 3596.
52. Carbene (Carbenoide), Vol. E19b (Ed.:, M. Regitz,) of Methoden der Organischen Chemie (Houben-Weyl), Thieme, Stuttgart, 1989
53. M. N. Protopopova, E. A. Shapiro, Russ. Chem. Rev. 1989, 58, 667
54. M. P. Doyle, M. A. McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides, Wiley, New York, 1998.
55. M. M. Díaz-Requejo, M. A. Mairena, T. R. Belderrain, M. C. Nicasio, S. Trofimenko, P. J. Pérez, Chem. Commun. 2001, 1804
56. A. Suárez, G. C. Fu, Angew. Chem. 2004, 116, 3664
57. Angew. Chem. Int. Ed. 2004, 43, 3580
58. M. P. Doyle, T. M. Weathers, Jr., Y. Wang, Adv. Synth. Catal. 2006, 348, 2403
59. M. Hassink, X. Liu, J. M. Fox, Org. Lett. 2011, 13, 2388
60. L. Zhou, J. Ma, Y. Zhang, J. Wang, Tetrahedron Lett. 2011, 52, 5484
61. L. Zhou, F. Ye, Y. Zhang, J. Wang, J. Am. Chem. Soc. 2010, 132, 13590
62. Q. Xiao, Y. Xia, H. Li, Y. Zhang, J. Wang, Angew. Chem. 2011, 123, 1146
63. Angew. Chem. Int. Ed. 2011, 50, 1114
64. L. Zhou, F. Ye, J. Ma, Y. Zhang, J. Wang, Angew. Chem. 2011, 123, 3572
65. Angew. Chem. Int. Ed. 2011, 50, 3510
66. F. Ye, X. Ma, Q. Xiao, H. Li, Y. Zhang, J. Wang, J. Am. Chem. Soc. 2012, 134, 5742.
67. H. E. Zimmerman, Acc. Chem. Res. 1971, 4, 272
68. K. N. Houk, Acc. Chem. Res. 1975, 8, 361
69. I. Fleming, Frontier Orbitals and Organic Chemical Reactions, Wiley, New York, 1976.