Palladium/copper-catalyzed sila-Sonogashira reactions of aryl iodides with alkynylsilanes via a direct C-Si bond activation

Tetrahedron Letters

Volumn 50, Issue 32, 2009, Pages 4643-4646

  Nishihara, Yasushi ^a   Inoue, Eiji ^a   Ogawa, Daisuke ^a   Okada, Yoshiaki ^a   Noyori, Shintaro ^a   Takagi, Kentaro ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; COPPER CHLORIDE; IODINE DERIVATIVE; PALLADIUM; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CROSS COUPLING REACTION; ELECTRON; SONOGASHIRA REACTION; STOICHIOMETRY;

EID: 67449101519     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.05.112     Document Type: Article

References (55)

1. Examples of recent reviews, see:. Sonogashira K. J. Organomet. Chem. 653 (2002) 46
2. Negishi E., and Anastasia L. Chem. Rev. 103 (2003) 1979
3. Nicolaou K.C., Bulger P.G., and Sarlah D. Angew. Chem., Int. Ed. 44 (2005) 4442
4. Yin L., and Liebscher J. Chem. Rev. 107 (2007) 133
5. Chinchilla R., and Nájera C. Chem. Rev. 107 (2007) 874
6. Sonogashira K. In: Diederich F., and Stang P.J. (Eds). Metal-Catalyzed Cross-Coupling Reactions (1998), Wiley-VCH, New York Chapter 5
7. Brandsma L., Vasilevsky S.F., and Verkruijsse H.D. Application of Transition Metal Catalysts in Organic Synthesis (1998), Springer, Berlin
8. Rossi R., Carpita A., and Bellina F. Org. Prep. Proced. Int. 27 (1995) 127-160
9. Sonogashira K. In: Trost B.M. (Ed). Comprehensive Organic Synthesis Vol. 3 (1991), Pergamon, New York Chapter 2.4
10. Ames D.E., Bull D., and Takundwa C. Synthesis (1981) 364
11. Menchi G., Scrivanti A., and Matteoli U. J. Mol. Chem. A: Chem. 152 (2000) 77
12. Mori A., Shimada T., Kondo T., and Sekiguchi A. Synlett (2001) 649
13. Mori A., Mohamed Ahmed M.S., Sekiguchi A., Masui K., and Koike T. Chem. Lett. (2002) 756
14. Mohamed Ahmed M.S., and Mori A. Tetrahedron 60 (2004) 9977
15. Mohamed Ahmed M.S., Sekiguchi A., Masui K., and Mori A. Bull. Chem. Soc. Jpn. 78 (2005) 160
16. Sonogashira K., Tohda Y., and Hagihara N. Tetrahedron Lett. (1975) 4467
17. Cassar L. J. Organomet. Chem. 93 (1975) 253
18. Dieck H.A., and Heck R.F. J. Organomet. Chem. 93 (1975) 259
19. Bohm V.P.W., and Herrmann W.A. Eur. J. Org. Chem. (2000) 3679
20. Pal M., Parasuraman K., Gupta S., and Yeleswarapu K.R. Synlett 14 (2002) 1976
21. Fukuyama T., Shinmen M., Nishitani S., Sato M., and Ryu I. Org. Lett. 4 (2002) 1691
22. Uozumi Y., and Kobayashi Y. Heterocycles 59 (2003) 71
23. Urgaonkar S., and Verkade J.G. J. Org. Chem. 69 (2004) 5752
24. Heuzé K., Méry D., Gauss D., Blais J.-C., and Astruc D. Chem. Eur. J. 10 (2004) 3936
25. Liang B., Dai M., Chen J., and Yang Z. J. Org. Chem. 70 (2005) 391
26. Liang B., Huang M., You Z., Xiong Z., Lu K., Fathi R., Chen J., and Yang Z. J. Org. Chem. 70 (2005) 6097
27. Cwik A.A., Hell Z., and Figueras F. Tetrahedron Lett. 47 (2006) 3023
28. Kawanami H., Matsushima K., Sato M., and Ikushima Y. Angew. Chem., Int. Ed. 46 (2007) 5129
29. Shi S., and Zhang Y. Synlett (2007) 1843
30. Ljungdahl T., Bennur T., Dallas A., Emtenaes H., and Maartensson J. Organometallics 27 (2008) 2490
31. Mori A., Kawashima J., Shimada T., Suguro M., Hirabayshi K., and Nishihara Y. Org. Lett. 2 (2000) 2935
32. Kobayashi K., Sugie A., Takahashi M., Masui K., and Mori A. Org. Lett. 7 (2005) 5083
33. Siemsen P., Livingston R.C., and Diederich F. Angew. Chem., Int. Ed. 39 (2000) 2632
34. Examples of recent reviews, see:. Littke A.F., and Fu G.C. Angew. Chem., Int. Ed. 41 (2002) 4176
35. Sonogashira K. J. Organomet. Chem. 653 (2002) 46
36. Negishi E.-I., and Anastasia L. Chem. Rev. 103 (2003) 1979
37. Rossi R., Carpita A., and Lezzi A. Tetrahedron 40 (1984) 2773
38. 3 and several other silver salts: see. Koseki Y., Omino K., Anzai S., and Nagasaka T. Tetrahedron Lett. 41 (2000) 2377
39. Nishihara Y., Ikegashira K., Mori A., and Hiyama T. Chem. Lett. (1997) 1233
40. Nishihara Y., Ikegashira K., Hirabayashi K., Ando J., Mori A., and Hiyama T. J. Org. Chem. 65 (2000) 1780
41. Nishihara Y., Inoue E., Okada Y., and Takagi K. Synlett (2008) 3041
42. The copper-free version of 'sila'-Sonogashira cross-coupling reaction has been achieved using a palladium/imidazolium salt system, see:. Yang C., and Nolan S.P. Organometallics 21 (2002) 1020
43. Hillier A.C., Grasa G.A., Viciu M.S., Lee H.M., Yang C., and Nolan S.P. J. Organomet. Chem. 653 (2002) 69
44. Examples for modified 'sila'-Sonogashira cross-coupling reaction under the basic conditions, see:. Marshall J.A., Chobanian H.R., and Yanik M.M. Org. Lett. 3 (2001) 4107
45. Mio M.J., Kopel L.C., Braun J.B., Gadzikwa T.L., Hull K.L., Brisbois R.G., Markworth C.J., and Grieco P.A. Org. Lett. 4 (2002) 3199
46. Gil-Moltóa J., and Nájera C. Adv. Synth. Catal. 348 (2006) 1874
47. Sørensen U.S., and Pombo-Villar E. Tetrahedron 61 (2005) 2697
48. Nishihara Y., Takemura M., Mori A., and Osakada K. J. Organomet. Chem. 620 (2001) 282
49. Nishihara Y., Okamoto M., Inoue Y., Miyazaki M., Miyasaka M., and Takagi K. Tetrahedron Lett. 46 (2005) 8661
50. Kang S.-K., Kim J.-S., and Choi S.-C. J. Org. Chem. 62 (1997) 4208
51. Hatanaka Y., and Hiyama T. J. Org. Chem. 53 (1988) 918
52. Hatanaka Y., Matsui K., and Hiyama T. Tetrahedron Lett. 30 (1989) 2403
53. Hirabayashi K., Mori A., Kawashima J., Suguro M., Nishihara Y., and Hiyama T. J. Org. Chem. 65 (2000) 5342
54. Chang S., Yang S.H., and Lee P.H. Tetrahedron Lett. 42 (2001) 4833
55. 3): δ 2.61 (s, 3H), 3.84 (s, 3H), 6.88-6.91 (m, 2H), 7.48-7.50 (m, 2H), 7.57-7.60 (m, 2H), 7.92-7.94 (m, 2H).