Platinum complex-catalyzed hydrosilylation and isomerization of methylenecyclopropane derivatives. Effect of structures of the substrate and catalyst

Journal of Organic Chemistry

Volumn 67, Issue 20, 2002, Pages 6889-6895

  Itazaki, Masumi ^a   Nishihara, Yasushi ^a   Osakada, Kohtaro ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROSILYLATION;

CATALYSIS; CATALYSTS; ISOMERIZATION; SUBSTRATES;

PLATINUM;

1,3 BUTADIENE DERIVATIVE; 2 METHYL 2 PHENYL 1 METHYLENECYCLOPROPANE; 2 PHENYL 1 METHYLENECYCLOPROPANE; 2,2 DIPHENYL 1 METHYLENECYCLOPROPANE; CARBENE; CYCLOPROPANE DERIVATIVE; PLATINUM COMPLEX; SILANE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ISOMERISM; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0037019970     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020293+     Document Type: Article

References (51)

1. (a) Brandi, A.; Goti,A. Chem. Rev. 1998, 98, 589-635.
2. (b) Binger, P.; Büch, H. M. Top. Curr. Chem. 1987, 135, 77-151.
3. (c) Ohta, T.; Takaya, H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p 1185.
4. 3Si-CN: Chatani, N.; Takeyasu, T.; Hanafusa, T. Tetrahedron Lett. 1988, 29, 3979-3982.
5. 3Sn-H: Lautens, M.; Meyer, C.; Lorenz, A. J. Am. Chem. Soc. 1996, 118, 10676-10677.
6. 2N-H: Tsukada, N.; Shibuya, A.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 8123-8124.
7. (b) Nakamura, I.; Itagaki, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 6458-6459.
8. (a) RO-H: Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. Angew. Chem., Int. Ed. 1999, 38, 3365-3367.
9. (b) Camacho, D. H.; Nakamura, I.; Saito, S.; Yamamoto, Y. J. Org. Chem. 2001, 66, 270-275.
10. 2: Ishiyama, T.; Momota, S.; Miyaura, N. Synlett 1999, 1790-1792.
11. 2: Suginome, M.; Matsuda, T.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 11015-11016.
12. 3Si-H: Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Yur'eva, N. M.; Beletskaya, I. P. J. Org. Chem. 1997, 62, 6069-6076.
13. Bessmertnykh, A. G.; Blinov, K. A.; Grishin, Yu. K.; Donskaya, N. A.; Tveritinova, E. V.; Beletskaya, I. P. Russ. J. Org. Chem. 1969, 34, 799-808.
14. Addition of silyl compounds to bicyclopropylidene without ring-opening has been achieved recently. See: Pohlmann, T.; de Meijere, A. Org. Lett. 2000, 2, 3877-3879.
15. RS-H, RS-SR: Xu, B.; Chen, Y.; Shi, M. Tetrahedron Lett. 2002, 43, 2781-2784.
16. (a) de Meijere, A.; Wessjohann, L. Synlett 1990, 20-32.
17. (b) Brandi, A.; Cordero, F. M.; de Sarlo, F.; Goti, A.; Guarna, A. Synlett 1993, 1-8.
18. Nishihara, Y.; Yoda, C.; Osakada, K. Organometallics 2001, 20, 2124-2126.
19. Nishihara, Y.; Itazaki, M.; Osakada, K. Tetrahedron Lett. 2002, 43, 2059-2061.
20. Drexler, J.; Lindermayer, R.; Hassan, M. A.; Sauer, J. Tetrahedron Lett. 1985, 26, 2555-2558.
21. Tamao, K.; Kakui, T.; Akita, M.; Iwahara, T.; Kanatani, R.; Yoshida, J.; Kumada, M. Tetrahedron 1983, 39, 983-990.
22. (a) Tamao, K.; Ishida, N.; Tanaka, T.; Kumada, M. Organome. tallics 1983, 2, 1694-1696.
23. (b) Tamao, K.; Ishida, N. J. Organomet. Chem. 1984, 269, C37-C39.
24. (c) Tamao, K.; Nakajo, E.; Ito, Y. J. Org. Chem. 1987, 52, 4412-4414.
25. (d) Tamao, K. In Organosilicon and Bioorganosilicon Chemistry; Sakurai, H., Ed.; Ellis Horwood: Chichester, 1985; pp 231-242.
26. Turnbull, M. D. Perkin Trans. 1 1997, 1241-1247.
27. As for the synthesis of cyclopropylmethylsilanes from allylsilanes, see: Fleming, I.; Sanderson, P. E.; Terrett, N. K. Synthesis 1992, 69-74.
28. For β-alkyl elimination of the late transition metal complexes, see: Murakami, M.; Ito, Y. In Activation of Unrective Bonds and Organic Synthesis; Murai, S., Eds; Springer-Verlag: Berlin, 1999; Vol. 3, pp 97-129.
29. (a) Thomson, S. K.; Young, G. B. Organometallics 1989, 8, 2068-2070.
30. (b) Thomas, B. J.; Noh, S. K.; Schulte, G. K.; Sendlinger, S. C.; Theopold, K. H. J. Am. Chem. Soc. 1991, 113, 893-902.
31. (c) Alkianiec, B.; Christou, V.; Hardy, D. T.; Thomson, S. K.; Young, G. B. J. Am. Chem. Soc. 1994, 116, 9963-9978.
32. (d) Suzuki, H.; Tanaka, M.; Takemori, T. J. Am. Chem. Soc. 1994, 116, 10779-10780.
33. (e) Rybtchinski, B.; Vigalok, A.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 1996, 118, 12406-12415.
34. (f) Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1989, 111, 2717-2719.
35. (g) McNeill, K.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1997, 119, 11244-11254.
36. (h) Kaplan, A. W.; Bergman, R. G. Organometallics 1997, 16, 1106-1108.
37. (a) Brown, J. M.; Kent, A. G. J. Chem. Soc., Perkin Trans. 2 1987, 1597-1607.
38. (b) Chiusoli, G. P.; Costa, M.; Meli, L. J. Organomet. Chem. 1988, 358, 495-505.
39. Grushin, V. V.; Akhrem, I. S.; Vol'pin M. E. J. Organomet. Chem. 1989, 371, 403-419.
40. 3 with IrX(CO)(dppe); see: Johnson, C. E.; Eisenberg, R. J. Am. Chem. Soc. 1985, 107, 6531-6540.
41. (a) Chalk, A. J.; Harrod, J. F. J. Am. Chem. Soc. 1965, 87, 16-21.
42. (b) Ojima, I.; Fuchikami, T.; Yatabe, M. J. Organomet. Chem. 1984, 260, 335-346.
43. (c) Sakaki, S.; Mizoe, N.; Sugimoto, M. Organometallics 1998, 17, 2510-2523.
44. Nishihara, Y.; Takemura, M.; Osakada, K. Organometallics 2002, 21, 825-831.
45. (a) Beesley, R. M.; Ingold, C. K.; Thorpe, J. F. J. Chem. Soc. 1915, 107, 1080-1106.
46. (b) Ingold, C. K. J. Chem. Soc., 1921, 119, 305, 951-970.
47. (c) Kon, G. A. R.; Steveson, A.; Thorpe, J. F. J. Chem. Soc. 1922, 121, 650-665.
48. Arona, S.; Binger P. Synthesis 1974, 801-803.
49. Kistner, C. R.; Hutchinson, J. H.; Doyle, J. R.; Storlie J. C. Inorg. Chem. 1963, 2, 1255-1261.
50. (a) Gerlach, D. H.; Kane, A. R.; Parshall, G. W.; Jesson, J. P.; Muetterties, E. L. J. Am. Chem. Soc. 1971, 93, 3543-3544.
51. (b) Yoshida, T.; Matsuda, T.; Otsuka, S. Inorg. Synth. 1979, 19, 107-110.