Regio- and stereoselective hydrosilylation of terminal alkynes using Grubbs' first-generation olefin-metathesis catalyst

Organic and Biomolecular Chemistry

Volumn 2, Issue 18, 2004, Pages 2558-2562

  Aricó, Caterina S ^a   Cox, Liam R ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; CATALYSIS; CATALYST ACTIVITY; CATALYSTS; CONDENSATION; HEATING; HYDROGEN; ISOMERS; REACTION KINETICS; REDUCTION; SILICON; SOLVENTS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CROSS-METATHESIS REACTIONS; HYDROSILYLATION; REACTION CONDITIONS; STEREOISOMERS;

HYDROCARBONS;

EID: 4744346552     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b409832c     Document Type: Article

References (54)

1. (a) I. Fleming, A. Barbero and D. Walter, Chem. Rev., 1997, 97, 2063-2192;
2. (b)E. Langkopf and D. Schinzer, Chem. Rev., 1995, 95, 135-1408;
3. (c) J. S. Panek, in Comprehensive Organic Synthesis, eds. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 1, pp 579-627;
4. (d) I. Fleming, J. Dunoguès and R. Smithers, Org. React. (N.Y.), 1989, 37, 57-575;
5. (e) T. A. Blumenkopf and L. E. Overman, Chem. Rev., 1986, 86, 857-873;
6. (f) T. H. Chan and I. Fleming, Synthesis, 1979, 761-786;
7. (g) Y. le, N. Chatani, T. Ogo, D. R. Marshall, T. Fukuyama, F. Kakiuchi and S. Murai, J. Org. Chem., 2000, 65, 1475-1488.
8. (a) S. E. Denmark, R. F. Sweis and D. Wehrli, J. Am. Chem. Soc., 2004, 126, 4865-4875;
9. (b) S. E. Denmark and R. F. Sweis, J. Am. Chem. Soc., 2004, 126, 4876-4882;
10. (c) S. E. Denmark and M. H. Ober, Aldrichimica Acta, 2003, 36, 75-85;
11. (d) S. E. Denmark and R. F. Sweis, Acc. Chem. Res., 2002, 35, 835-846;
12. (e) T. Hiyama and E. Shirakawa, Top. Curr. Chem., 2002, 219, 61-85.
13. (a) S. E. Denmark and S.-M.Yang, Org. Lett., 2001, 3, 1749-1752;
14. (b) A. G. M. Barrett, J. C. Beall, D. C. Braddock, K. Flack, V. C. Gibson and M. M. Salter, J. Org. Chem., 2000, 65, 6508-6514;
15. (c) S. Chang and R. H. Grubbs, Tetrahedron Lett., 1997, 38, 4757-4760.
16. (a) C. Pietraszuk, B. Marciniec and H. Fischer, Tetrahedron Lett., 2003, 44, 7121-7124;
17. (b) C. Pietraszuk, H. Fischer, M. Kujawa and B. Marciniec, Tetrahedron Lett., 2001, 42, 1175-1178;
18. (c) A. K. Chatterjee, J. P. Morgan, M. Scholl and R. H. Grubbs, J. Am. Chem. Soc., 2000, 122, 3783-3784.
19. (a) K. Oshima, in Science of Synthesis, ed. I. Fleming, Georg Thieme Verlag, New York, 2002, vol. 4, pp 713-756;
20. (b) F. Kakiuchi, A. Yamada, N. Chatani, S. Murai, N. Furukawa and Y. Seki, Organometallics, 1990, 18, 2033-2036;
21. (c) F. Kakiuchi, Y. Tanaka, N. Chatani and S. Murai, J. Organomet. Chem., 1993, 456, 45-47.
22. (a) T. Hiyama and T. Kusumoto, in Comprehensive Organic Synthesis, eds. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, vol. 8, pp 769-773;
23. (b) J. L. Speier, Adv. Organomet. Chem., 1979, 17, 407-447.
24. J. L. Speier, J. A. Webster and G. H. Barnes, J. Am. Chem. Soc., 1957, 79, 974-979.
25. For some recent examples involving Rh complexes: (a) A. Mori, E. Takahisa, Y. Yamamura, T. Kato, A. P. Mudalige, H. Kajiro, K. Hirabayashi, Y. Nishihara and T. Hiyama, Organometallics, 2004, 23, 1755-1765; (b) R. Takeuchi and N. Tanouchi, J. Chem. Soc., Perkin Trans. 1, 1994, 2909-2913; (c) I. Ojima, N. Clos, R. J. Donovan and P. Ingallina, Organometallics, 1990, 9, 3127-3133; (d) For a comprehensive review: I. Ojima, Z. Li and J. Zhu, in The Chemistry of Organosilicon Compounds, eds. Z. Rappoport and Y. Apeloig, John Wiley and Sons, Chichester, 1998, Volume 2, Chapter 29, pp 1687-1792.
26. For some recent examples involving Rh complexes: (a) A. Mori, E. Takahisa, Y. Yamamura, T. Kato, A. P. Mudalige, H. Kajiro, K. Hirabayashi, Y. Nishihara and T. Hiyama, Organometallics, 2004, 23, 1755-1765; (b) R. Takeuchi and N. Tanouchi, J. Chem. Soc., Perkin Trans. 1, 1994, 2909-2913; (c) I. Ojima, N. Clos, R. J. Donovan and P. Ingallina, Organometallics, 1990, 9, 3127-3133; (d) For a comprehensive review: I. Ojima, Z. Li and J. Zhu, in The Chemistry of Organosilicon Compounds, eds. Z. Rappoport and Y. Apeloig, John Wiley and Sons, Chichester, 1998, Volume 2, Chapter 29, pp 1687-1792.
27. For some recent examples involving Rh complexes: (a) A. Mori, E. Takahisa, Y. Yamamura, T. Kato, A. P. Mudalige, H. Kajiro, K. Hirabayashi, Y. Nishihara and T. Hiyama, Organometallics, 2004, 23, 1755-1765; (b) R. Takeuchi and N. Tanouchi, J. Chem. Soc., Perkin Trans. 1, 1994, 2909-2913; (c) I. Ojima, N. Clos, R. J. Donovan and P. Ingallina, Organometallics, 1990, 9, 3127-3133; (d) For a comprehensive review: I. Ojima, Z. Li and J. Zhu, in The Chemistry of Organosilicon Compounds, eds. Z. Rappoport and Y. Apeloig, John Wiley and Sons, Chichester, 1998, Volume 2, Chapter 29, pp 1687-1792.
28. For some recent examples involving Rh complexes: (a) A. Mori, E. Takahisa, Y. Yamamura, T. Kato, A. P. Mudalige, H. Kajiro, K. Hirabayashi, Y. Nishihara and T. Hiyama, Organometallics, 2004, 23, 1755-1765; (b) R. Takeuchi and N. Tanouchi, J. Chem. Soc., Perkin Trans. 1, 1994, 2909-2913; (c) I. Ojima, N. Clos, R. J. Donovan and P. Ingallina, Organometallics, 1990, 9, 3127-3133; (d) For a comprehensive review: I. Ojima, Z. Li and J. Zhu, in The Chemistry of Organosilicon Compounds, eds. Z. Rappoport and Y. Apeloig, John Wiley and Sons, Chichester, 1998, Volume 2, Chapter 29, pp 1687-1792.
29. For some recent examples involving Ru complexes: (a) Y. Kawanami, Y. Sonoda, T. Mori and K. Yamamoto, Org. Lett., 2002, 4, 2825-2827; (b) B. M. Trost and Z. T. Ball, J. Am. Chem. Soc., 2001, 123, 12726-12727;
30. For some recent examples involving Ru complexes: (a) Y. Kawanami, Y. Sonoda, T. Mori and K. Yamamoto, Org. Lett., 2002, 4, 2825-2827; (b) B. M. Trost and Z. T. Ball, J. Am. Chem. Soc., 2001, 123, 12726-12727;
31. (c) Y. Na and S. Chang, Org. Lett., 2000, 2, 1887-1889.
32. (a) T. M. Trnka and R. H. Grubbs, Acc. Chem. Res., 2001, 34, 18-29;
33. (b) A. Fürstner, Angew. Chem., Int. Ed., 2000, 39, 3012-3043;
34. (c) R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413-4450;
35. (d) S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371-388.
36. B. Alcaide and P. Almendros, Chem. Eur. J., 2003, 9, 1258-1262.
37. S. V. Maifeld, R. L. Miller and D. Lee, Tetrahedron Lett., 2002, 43, 6363-6366.
38. In subsequent reactions stopping the reaction as soon as all starting material had been consumed minimised this problem.
39. C-Si bond length ∼1.85 Å; C-C bond length ∼1.54 Å.
40. (a) T. Murai, F. Kimura, K. Tsutsui, K. Hasegawa and S. Kato, Organometallics, 1998, 17, 926-932;
41. (b) G. Stork, M. E. Jung, E. Colvin and Y. Noel, J. Am. Chem. Soc., 1974, 96, 3684-3686.
42. (a) J. L. Herrisson and Y. Chauvin, Makromol. Chem., 1970, 141, 161-176;
43. (b) for a recent discussion of the mechanism of olefin metathesis see: C. Adlhart and P. Chen, J. Am. Chem. Soc., 2004, 126, 3496-3510.
44. (a) H. Katayama, K. Taniguchi, M. Kobayashi, T. Sagawa, T. Minami and F. Ozawa, J. Organomet. Chem., 2002, 645, 192-200;
45. (b) S. M. Maddock, C. E. F. Rickard, W. R. Roper and L. J. Wright, Organometallics, 1996, 15, 1793-1803;
46. (c) C.-H. Jun and R. H. Crabtree, J. Organomet. Chem., 1993, 447, 177-187;
47. (d) M. A. Esteruelas, J. Herrero and L. A. Oro, Organometallics, 1993, 12, 2377-2379;
48. (e) R. S. Tanke and R. H. Crabtree, J. Am. Chem. Soc., 1990, 112, 7984-7989.
49. M. Ulman and R. H. Grubbs, J. Org. Chem., 1999, 64, 7202-7207.
50. B. Schmidt, Synlett, 2004, 1541-1544 and references therein.
51. B. Schmidt, Eur. J. Org. Chem., 2004, 1865-1880.
52. A. J. Chalk and J. F. Harrod, J. Am. Chem. Soc., 1965, 87, 16-21.
53. L. W. Chung, Y.-D. Wu, B. M. Trost and Z. T. Ball, J. Am. Chem. Soc., 2003, 125, 11578-11582.
54. J. M. Brown, Chem. Soc. Rev., 1993, 22, 25-41.