Hydrosilylation of alkynes catalyzed by ruthenium carbene complexes

Tetrahedron Letters

Volumn 46, Issue 1, 2005, Pages 105-108

  Maifeld, Sarah V ^a   Tran, Michael N ^a   Lee, Daesung ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Alkyne; Catalysis; Hydrosilylation; Ruthenium; Vinylsilane

Indexed keywords

ALKYNE DERIVATIVE; HYDROXYL GROUP; RUTHENIUM COMPLEX; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CIS ISOMER; HYDROSILYLATION; ISOMER;

EID: 10044251035     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.025     Document Type: Article

References (61)

1. For reviews, see: A. Deiters, and S.F. Martin Chem. Rev. 104 2004 2199
2. A.J. Giessert, and S.T. Diver Chem. Rev. 104 2004 1317
3. C.S. Poulsen, and R. Madsen Synthesis 2003 1
4. M. Mori R.H. Grubbs Handbook of Metathesis Vol. 2 2003 Wiley-VCH Weinheim, Germany 176 204
5. S.J. Connon, and S. Blechert Angew. Chem., Int. Ed. 42 2003 1900
6. R.R. Shrock, and A.H. Hoveyda Angew. Chem., Int. Ed. 42 2003 4592
7. A. Furstner Angew. Chem., Int. Ed. 39 2000 3013
8. R.H. Grubbs, and S. Chang Tetrahedron 54 1998 4413
9. P. Schwab, M.B. France, J.W. Ziller, and R.H. Grubbs Angew. Chem., Int. Ed. 34 1995 2039
10. Z. Wu, S.T. Nguyen, R.H. Grubbs, and J.W. Ziller J. Am. Chem. Soc. 117 1995 5503
11. P. Schwab, R.H. Grubbs, and J.W. Ziller J. Am. Chem. Soc. 118 1996 100
12. M. Scholl, S. Ding, C.W. Lee, and R.H. Grubbs Org. Lett. 1 1999 953
13. C.W. Lee, and R.H. Grubbs Org. Lett. 2 2000 2558
14. For examples of nonmetathesis behavior of Grubbs-type carbenes, see: B. Alcaide, and P. Almendros Chem. Eur. J. 9 2003 1258 and references cited therein
15. M. Mori, N. Saito, D. Tanaka, M. Takimoto, and Y. Sato J. Am. Chem. Soc. 125 2003 5606
16. P. Quayle, D. Fengas, and S. Richards Synlett 2003 1797
17. B. Schmidt Angew. Chem., Int. Ed. 42 2003 4996
18. T. Kitamura, Y. Sato, and M. Mori Chem. Commun. 2001 1258
19. F. Lopez, A. Delgado, J.R. Rodriguez, L. Castedo, and J.L. Mascarenas J. Am. Chem. Soc. 126 2004 10262
20. S.V. Maifeld, R.L. Miller, and D. Lee Tetrahedron Lett. 43 2002 6363
21. I. Ojima, Z. Li, and J. Zhu S. Rappoport Y. Apeloig The Chemistry of Organosilicon Compounds 1998 Wiley New York
22. E. Langkopf, and D. Schinzer Chem. Rev. 95 1995 135
23. T. Hiyama, and T. Kusumoto B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 8 1991 Pergamon Oxford 763
24. I. Ojima S. Patai Z. Rappoport The Chemistry of Organic Silicon Compounds 1989 John Wiley Chichester 1479
25. B. Marciniec Comprehensive Handbook on Hydrosilylation 1992 Pergamon Oxford
26. I. Fleming, J. Dungogues, and R.H. Smithers Org. React. 37 1989 57
27. A. Sato, H. Kinoshita, H. Shinokubo, and K. Oshima Org. Lett. 6 2004 2217
28. J.W. Faller, and D.G. D'Alliessi Organometallics 21 2002 1743
29. R. Takeuchi, and I. Ebata Organometallics 16 1997 3707
30. R. Takeuchi, S. Nitta, and D. Watanabe J. Org. Chem. 60 1995 3045
31. L.D. Field, and A.J. Ward J. Organomet. Chem. 681 2003 91
32. M.P. Doyle, K.G. High, C.L. Nesloney, T.W. Clayton Jr., and J. Lin Organometallics 10 1991 1225
33. I. Ojima, N. Clos, R.J. Donovan, and P. Ingallina Organometallics 9 1990 3127
34. H. Watanabe, T. Kitahara, R. Motegi, and Y. Nagai J. Organomet. Chem. 139 1977 215
35. J.E. Hill, and T.A. Nile J. Organomet. Chem. 137 1977 293
36. I. Ojima, M. Kumafai, and Y. Hagai J. Organomet. Chem. 137 1977 293
37. I. Ojima, and M. Kumagi J. Organomet. Chem. 66 1974 C14
38. M. Martin, E. Sola, O. Torres, P. Plou, and L.A. Oro Organometallics 22 2003 5406
39. C. Jun, and R.H. Crabtree J. Organomet. Chem. 447 1993 177
40. R.S. Tanke, and R.H. Crabtree J. Am. Chem. Soc. 112 1990 7984
41. Y. Na, and S. Chang Org. Lett. 4 2002 2825
42. Y. Kawanami, Y. Sonoda, T. Mori, and K. Yamamoto Org. Lett. 4 2002 2825
43. H. Katayama, K. Taniguchi, M. Kobayashi, T. Sagawa, T. Minami, and F. Ozawa J. Organomet. Chem. 645 2002 192
44. Z.T. Ball, and B.M. Trost J. Am. Chem. Soc. 123 2001 12726
45. K. Itami, K. Mitsudo, A. Nishino, and J.-i. Yoshida J. Org. Chem. 67 2002 2645
46. H. Matsumoto, Y. Hoshino, and Y. Nagai Chem. Lett. 1982 1663
47. Grimm, J. B.; Lee, D. J. Org. Chem. 2004, published on web 06-Nov-2004, doi:10.1021/jo0489081
48. S.V. Maifeld, R.L. Miller, and D. Lee J. Am. Chem. Soc. 126 2004 10242
49. R.L. Miller, S.V. Maifeld, and D. Lee Org. Lett. 6 2004 2773
50. A competitive silylation experiment employing equimolar amounts of 1-hexyne, 1-propanol, and dimethylsilane revealed a 4.5:1 relative ratio of carbon-carbon triple bond hydrosilylation over oxygen silylation
51. Alcohol (2 equiv) and silane (1 equiv) were employed to restrict the formation of minor amounts of silyl ether as well as hydrosilylated silyl ether
52. J. Huang, E.D. Stevens, S.P. Nolan, and J.L. Petersen J. Am. Chem. Soc. 121 1999 2674
53. J. Huang, H.-J. Schanz, E.D. Stevens, and S.P. Nolan Organometallics 18 1999 5375
54. A. Furstner, O.R. Thiel, L. Ackermann, H.-J. Schanz, and S.P. Nolan J. Org. Chem. 65 2000 2204
55. M. Scholl, T.M. Trnka, J.P. Morgan, and R.H. Grubbs Tetrahedron Lett. 40 1999 2247
56. R. Dorta, R.A. Kelly III, and S.P. Nolan Adv. Synth. Catal. 346 2004 917
57. L. Jafarpour, H.-J. Schanz, E.D. Stevens, and S.P. Nolan Organometallics 18 1999 5416
58. K. Melis, D. De Vos, P. Jacobs, and F. Verpoort J. Organomet. Chem. 659 2002 159
59. For Z-stereoselective intramolecular hydrosilylation followed by silicon-assisted cross-coupling reactions, see: S.E. Denmark, and W. Pan Org. Lett. 4 2002 4163
60. For E-stereoselective intramolecular hydrosilylation followed by silicon-assisted cross-coupling reactions, see: S. Denmark, and W. Pan Org. Lett. 3 2001 361
61. 1H NMR experiments employing a variety of silanes at various temperatures in the absence of alkyne have been attempted to identify this metal hydride intermediate; however, the observation of this complex has been precluded by the formation of silyl byproducts, presumably arising from silyl condensation