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니켈 촉매를 이용한 1,1'-Bis(dimethylsilyl)ferrocene과 Carbonyl 화합물의 Silylation 반응

Nickel Catalyzed Silylation Reaction of Carbonyl Compounds with 1,1'-Bis(dimethylsilyl)ferrocene

  • 공영건 (경기대학교 자연과학부 화학과) ;
  • 이정현 (경기대학교 자연과학부 화학과)
  • 발행 : 2002.04.20

초록

니켈 착물을 촉매로 사용한 1,1´-Bis(dimethylsilyl)ferrocene [1]과 carbonyl 화합물 -benzaldehyde, 4-cyanobenzaldehyde, trimethylacetaldehyde, acetophenone과 benzophenone-은 3-oxa-2,5-disilacyclo-1,1′-ferrocene을 생성하였다. 이와 대비되게 동일한 반응조건에서 화합물 [1]과 isobutyraldehyde의 반응에는 1,1′-bis(dimethylsilyl)ferrocene의 Si-H 결합에 2개의 aldehyde ligand가 이중 삽입된 생성물이 형성되었다.

The nickel-catalyzed reation of 1,1'-bis(dimethysilyl)ferrocene[1] with carbonyls such as benzaldehyde, 4-cyaonbezaldehyde, trimethylacetaldehyde, acethon, and benzophenone afforded 3-oxa-2,5-disilacyclo-1,1'-ferrocene. In contrast, the reation of [1] with isobutyraldehyde under the same reation condition yielded the diinsertion products formed via the insertion of two aldehyde ligands into the Si-H bond of 1,1'-bis(dimethy)ferrocene.

키워드

참고문헌

  1. Patai, S.; Rappoport, Z. The Chemistry of Organic Silicon Compounds, Eds.; John Wiley & Sons, 1989
  2. Belestskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435. https://doi.org/10.1021/cr9902594
  3. Shatma, H. K.; Pannell, K. H. Chem. Rev. 1995, 95, 1351. https://doi.org/10.1021/cr00037a010
  4. Braunstein, P.; Knorr, M. J. Organoment. Chem. 1995, 500, 21. https://doi.org/10.1016/0022-328X(95)00530-4
  5. Okinoshima, H.; Yamamoto, K.; Kumada, M. J. Organomet. Chem. 1975. 86, C27. https://doi.org/10.1016/S0022-328X(00)89623-0
  6. Seyferth, D.; Goldman, E. W.; Escue, J. J. Organomet. Chem. 1984, 271, 337 https://doi.org/10.1016/0022-328X(84)85187-6
  7. Yamashita, H.; Catellani, M.; Tanaka, M. Chem. Lett. 1991, 241.
  8. Murakami, M.; Andersson, P. G.; Andersson, P. G.; Suginome, M.; Ito, Y. J. Am. Chem. Soc. 1991, 113, 3987. https://doi.org/10.1021/ja00010a049
  9. Sakurai, H.; Kamiyama, Y.; Nakadaira, Y. J. Am. Chem. Soc. 1975, 97, 931. https://doi.org/10.1021/ja00837a061
  10. Carson, C. W.; West, R. Organometallics 1983, 2, 1081.
  11. Eaborn, C.; Metham, T. N.; Pidcock, A. J. Organomet. Chem. 1973, 63, 107. https://doi.org/10.1016/S0022-328X(73)80024-5
  12. Tanaka, M.; Uchimaru, Y. Bull. Soc. Chem. Fr. 1992, 129, 667.
  13. Fink, W. Helv. Chim. Acta. 1976, 59, 60.
  14. Ishikawa, M.; Okazaki, S.; Naka, A.; Tachibana, A.; Kawauchi, S.; Yamabe, T. Organometallics 1995, 14, 114. https://doi.org/10.1021/om00001a020
  15. Naka, A.; Okazaki, S.; Hayashi, M.; Ishikawa, M. J. Organomet. Chem. 1995, 499, 35. https://doi.org/10.1016/0022-328X(95)00329-O
  16. Ishikawa, M.; Ohshita, J.;Ito, Y. Organometallics 1986, 5, 1518.
  17. Ishikawa, M.; Sakamoto, H.; Okazaki, S.; Naka, A. J. Organomet. Chem. 1992, 439, 19. https://doi.org/10.1016/0022-328X(92)80049-4
  18. Ishikawa, M.; Okazaki, S.; Naka, A.; Sakamoto, H. Organometallics 1992, 11, 4135. https://doi.org/10.1021/om00060a033
  19. Ishikawa, M.; Naka, A.; Okazaki, S.; Sakamoto, H. Organometallics 1993, 12, 87. https://doi.org/10.1021/om00025a018
  20. Kang, Y.; Lee, J.; Kong, Y. K.; Kang, S. O.; Ko, J. Organometallics 2000, 19, 1722. https://doi.org/10.1021/om990915q
  21. Kang, Y.; Kim, J.; Kong, Y. K.; Lee, J.; Lee, S. W.; Kang, S. O.; Ko, J. Organometallics 2000, 19, 5026. https://doi.org/10.1021/om000527k
  22. Rausch, M. D.; Ciappenelli, D. J. J. Orgamet. Chem. 1967, 10, 127. https://doi.org/10.1016/S0022-328X(00)81725-8
  23. Cundy, C. S. J. Organomet. Chem. 1974, 69, 305. https://doi.org/10.1016/S0022-328X(00)90250-X
  24. Finckh, W.; Tang, B.; Lough, A.; Manners, I. Organometallics 1992, 11, 2904 https://doi.org/10.1021/om00044a034
  25. Uchimaru, Y.; Latenschlager, H.-J.; Wynd, A. J.; Tanaka, M. Organometallics 1992, 11, 2639. https://doi.org/10.1021/om00043a056

피인용 문헌

  1. Hydrosilylation and double silylation of carbonyl compounds with 1,1′-bis(dimethylsilyl)ferrocene using nickel- and platinum-catalysts vol.48, pp.11, 2007, https://doi.org/10.1016/j.tetlet.2007.01.009
  2. 니켈/백금 촉매에 의한 1,1'-Bis(dimethylsilyl)ferrocene과 Aldehydes의 선택적 Silylation 반응 vol.51, pp.3, 2002, https://doi.org/10.5012/jkcs.2007.51.3.232
  3. 백금/니켈 촉매를 이용한 1,1'-Bis(dimethylhydrosilyl)ferrocene과 Alkynes, Alkenes의 선택적 Hydrosilyation 반응 vol.54, pp.1, 2002, https://doi.org/10.5012/jkcs.2010.54.01.027