Copper-free palladium-catalyzed sonogashira-type coupling of aryl halides and 1-aryl-2-(trimethylsilyl)acetylenes

Tetrahedron

Volumn 61, Issue 10, 2005, Pages 2697-2703

  Sørensen, Ulrik S ^a   Pombo Villar, Esteban ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

1 Aryl 2 trimethylsilylacetylenes; Diaryl acetylenes; Microwaves; Sonogashira type coupling

Indexed keywords

ACETYLENE DERIVATIVE; COPPER; HALIDE; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; DIELECTRIC CONSTANT; PRIORITY JOURNAL; REACTION ANALYSIS; SONOGASHIRA REACTION; TEMPERATURE SENSITIVITY;

EID: 13944265590     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.01.032     Document Type: Article

References (52)

1. K. Sonogashira, Y. Tohda, and N. Hagihara Tetrahedron Lett. 1975 4467 4470
2. S. Takahashi, Y. Kuroyama, K. Sonogashira, and N. Hagihara Synthesis 1980 627 630
3. E.-i. Negishi, and L. Anastasia Chem. Rev. 103 2003 1979 2017
4. H.A. Dieck, and F.R. Heck J. Organomet. Chem. 93 1975 259 263
5. L. Cassar J. Organomet. Chem. 93 1975 253 257
6. W.B. Austin, N. Bilow, W.J. Kelleghan, and K.S.Y. Lau J. Org. Chem. 46 1981 2280 2286
7. R. Rossi, A. Carpita, and F. Bellina Org. Prep. Proced. Int. 27 1995 127 160
8. J.-F. Nguefack, V. Bolitt, and D. Sinou Tetrahedron Lett. 37 1996 5527 5530
9. V.P.W. Böhm, and W.A. Herrmann Eur. J. Org. Chem. 2000 3679 3681
10. T. Fukuyama, M. Shinmen, S. Nishitani, M. Sato, and I. Ryu Organic Lett. 4 2002 1691 1694
11. P. Siemsen, R.C. Livingston, and F. Diederich Angew. Chem. Int. Ed. Engl. 39 2000 2632 2657
12. A.B. Dyatkin, and R.A. Rivero Tetrahedron Lett. 39 1998 3647 3650
13. S. Huang, and J.M. Tour J. Am. Chem. Soc. 121 1999 4908 4909
14. Preliminary results on this work have previously been published in two posters: (a) Sørensen, U. S.; Wede, J.; Pombo-Villar, E. 5th Electronic Conf. Synth. Org. Chem. 2001 http://www.mdpi.net/ecsoc-5/e0019/e0019.htm. (b) Sørensen, U. S.; Wede, J.; Pombo-Villar, E. 12th Eur. Symposium Org. Chem. 2001, abstract P2-124.
15. Preliminary results on this work have previously been published in two posters: (a) Sørensen, U. S.; Wede, J.; Pombo-Villar, E. 5th Electronic Conf. Synth. Org. Chem. 2001 http://www.mdpi.net/ecsoc-5/e0019/e0019.htm. (b) Sørensen, U. S.; Wede, J.; Pombo-Villar, E. 12th Eur. Symposium Org. Chem. 2001, abstract P2-124.
16. Y. Koseki, K. Omino, S. Anzai, and T. Nagasaka Tetrahedron Lett. 41 2000 2377 2380
17. U. Halbes, and P. Pale Tetrahedron Lett. 43 2002 2039 2042
18. Y. Nishihara, K. Ikegashira, K. Hirabayashi, J.-i. Ando, A. Mori, and T. Hiyama J. Org. Chem. 65 2000 1780 1787
19. R. Rossi, A. Carpita, and A. Lezzi Tetrahedron 40 1984 2773 2779
20. R.N. Gedye, W. Rank, and K.C. Westaway Can. J. Chem. 69 1991 706 711
21. J.A. Marshall, H.R. Chobanian, and M.M. Yanik Org. Lett. 3 2001 4107 4110
22. R.A. Abramovitch Org. Prep. Proced. Int. 23 1991 683 711
23. D.M.P. Mingos, and D. Baghurst Chem. Soc. Rev. 20 1991 1 47
24. C.R. Strauss, and R.W. Trainor Aust. J. Chem. 48 1995 1665 1692
25. S. Caddick Tetrahedron 51 1995 10403 10432
26. S.A. Galema Chem. Soc. Rev. 26 1997 233 238
27. F. Langa, P.D.L. Cruz, A.D.L. Hoz, A. Díaz-Ortiz, and E. Díez-Barra Contemp. Org. Synth. 4 1997 373 386
28. P. Lidström, J. Tierney, B. Wathey, and J. Westman Tetrahedron 57 2001 9225 9283
29. N. Kuhnert Angew. Chem. Int. Ed. Engl. 41 2002 1863 1866
30. M. Erdélyi, and A. Gogoll J. Org. Chem. 66 2001 4165 4169
31. F. Gasparini, K. Lingenhöhl, N. Stoehr, P.J. Flor, M. Heinrich, I. Vranesic, M. Biollaz, H. Allgeier, R. Heckendorn, S. Urwyler, M.A. Varney, E.C. Johnson, S.D. Hess, S.P. Rao, A.I. Sacaan, E.M. Santori, G. Veliçelebi, and R. Kuhn Neuropharmacology 38 1999 1493 1503
32. T.E. Salt, K.E. Binns, J.P. Turner, F. Gasparini, and R. Kuhn Br. J. Pharmacol. 127 1999 1057 1059
33. I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009 3066
34. C. Amatore, E. Carré, A. Jutand, and M.A. M'Barki Organometallics 14 1995 1818 1826
35. N.G. Kundu, M. Pal, and B. Nandi J. Chem. Soc., Perkin Trans. 1 1 1998 561 568
36. T. Sakamoto, Y. Kondo, R. Watanabe, and H. Yamanaka Chem. Pharm. Bull. 34 1986 2719 2724
37. K. Edo, T. Sakamoto, and H. Yamanaka Chem. Pharm. Bull. 26 1978 3843 3850
38. S.E. Denmark, and S.A. Tymonko J. Org. Chem. 68 2003 9151 9154
39. K. Itami, T. Nokami, and J.-i. Yoshida J. Am. Chem. Soc. 123 2001 5600 5601
40. T. Hiyama, and Y. Hatanaka Pure Appl. Chem. 66 1994 1471 1478 and references cited therein
41. N. Morita, and S.I. Miller J. Org. Chem. 42 1977 4245 4248
42. A. Fürstner, and G. Seidel Tetrahedron 51 1995 11165 11176
43. J. Okubo, H. Shinozaki, T. Koitabashi, and R. Yomura Bull. Chem. Soc. Jpn. 71 1998 329 335
44. H. Sashida, M. Kato, and T. Tsuchiya Chem. Pharm. Bull. 36 1988 3826 3832
45. R. Beugelmans, and M. Bois-Choussy Heterocycles 26 1987 1863 1871
46. W. Shen, and L. Wang J. Org. Chem. 64 1999 8873 8879
47. A.V. Vasil'ev, and A.P. Rudenko Russ. J. Org. Chem. 33 1997 1555 1584
48. S.-K. Kang, J.-S. Kim, S.-K. Yoon, K.-H. Lim, and S.S. Yoon Tetrahedron Lett. 39 1998 3011 3012
49. K. Okuro, M. Furuune, M. Enna, M. Miura, and M. Nomura J. Org. Chem. 58 1993 4716 4721
50. A. Padwa, U. Chiacchio, D.J. Fairfax, J.M. Kassir, A. Litrico, M.A. Semones, and S.L. Xu J. Org. Chem. 58 1993 6429 6437
51. S. Cacchi, V. Carnicelli, and F. Marinelli J. Organomet. Chem. 1994 289 296
52. T. Teitel, D. Wells, and W.H.F. Sasse Aust. J. Chem. 26 1973 2129 2146