Nickel-catalyzed reactions of silacyclobutanes with aldehydes: Ring opening and ring expansion reaction

Organic Letters

Volumn 8, Issue 3, 2006, Pages 483-485

  Hirano, Koji ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 32644446485     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0527577     Document Type: Article

References (32)

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18. 2 did not catalyze the reaction.
19. In the Suzuki-Miyaura cross-coupling reactions, the same tendency was observed. See: Netherton, M. R.; Dai, C.; Neuschütz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099-10100.
20. Silacyclobutanes were found to undergo oxidative addition to platinum and palladium complexes. (a) Yamashita, H.; Tanaka, M.; Honda, K. J. Am. Chem. Soc. 1995, 117, 8873-8874.
21. (b) Tanaka, Y.; Yamashita, H.; Shimada, S.; Tanaka, M. Organometallics 1997, 16, 3246-3248.
22. Nickel-catalyzed hydrosilylations of aldehydes and imines are quite rare. See: (a) Lappert, M. F.; Nile, T. A. J. Organomet. Chem. 1975, 102, 543-550.
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25. 2-Coordinated nickel complexes with aldehydes have been reported, (a) Ogoshi, S.; Oka, M.; Kurosawa, H. J. Am. Chem. Soc. 2004, 126, 11802-11803. The intermediate 5 or 6 was suggested in other nickel-catalyzed reactions,
26. (b) Biswas, K.; Prieto, O.; Goldsmith, P. J.; Woodward, S. Angew. Chem., Int. Ed. 2005, 44, 2232-2234.
27. (c) Hirano, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2005, 7, 4689-4691. Nevertheless, oxidative addition of silacyclobutanes to palladium complexes is found to be an equilibrium reaction. Hence, it is also probable that initial oxidative addition of 1a to 4 followed by subsequent direct insertion of 2a generates 7. See ref 9b.
28. The reaction of 5 with TMSOTf can promote the formation of the covalent bond between nickel and carbonyl carbon with the aid of the Lewis acidity of silicon. See ref 11a. Thus, it seems quite possible that this transmetalation would include a similar intermediate.
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