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Volumn 127, Issue 21, 2005, Pages 7805-7814

Ruthenium-catalyzed ionic hydrogenation of iminium cations. Scope and mechanism

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSIS; CATALYSTS; CHELATION; IONIC CONDUCTION; RUTHENIUM COMPOUNDS; STOICHIOMETRY;

EID: 19744370551     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0506861     Document Type: Article
Times cited : (145)

References (90)
  • 1
    • 0000696874 scopus 로고    scopus 로고
    • Hydrogenation of Imine Groups; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: New York
    • Reviews on the asymmetric hydrogenation of C=N: (a) Blaser, H.-U.; Spindler, F. Hydrogenation of Imine Groups. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: New York, 1999; Vol. 1, pp 247-265.
    • (1999) Comprehensive Asymmetric Catalysis , vol.1 , pp. 247-265
    • Blaser, H.-U.1    Spindler, F.2
  • 2
    • 7044252416 scopus 로고    scopus 로고
    • Hydrogenation of Imino Groups; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin
    • (b) Ohkuma, T.; Noyori, R. Hydrogenation of Imino Groups. In Comprehensive Asymmetric Catalysis, Supplement; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 2004; Vol. 1, pp 43-53.
    • (2004) Comprehensive Asymmetric Catalysis, Supplement , vol.1 , pp. 43-53
    • Ohkuma, T.1    Noyori, R.2
  • 5
    • 0000811037 scopus 로고
    • A chiral titanocene catalyst that gives high ee's only for the hydrogenation of cyclic imines: (a) Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1992, 114, 7562-7564.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 7562-7564
    • Willoughby, C.A.1    Buchwald, S.L.2
  • 9
  • 11
    • 0032540968 scopus 로고    scopus 로고
    • An Ir catalyst that gives high ee's with acyclic imines that have bulky substituents on N: (a) Zhu, G.; Zhang, X. Tetrahedron: Asymmetry 1998, 9, 2415-2418.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 2415-2418
    • Zhu, G.1    Zhang, X.2
  • 14
    • 8344272116 scopus 로고    scopus 로고
    • 2H (PTA = 1,3,5-triaza-7-phosphaadamantane), has just been isolated and characterized: (a) Frost, B. J.; Mebi, C. A. Organometallics 2004, 23, 5317-5323. The same hydride has also been observed in solution:
    • (2004) Organometallics , vol.23 , pp. 5317-5323
    • Frost, B.J.1    Mebi, C.A.2
  • 47
    • 19744363643 scopus 로고    scopus 로고
    • note
    • 2 cation.
  • 49
    • 0142008881 scopus 로고    scopus 로고
    • Guan, H.; Iimura, M.; Magee, M. P.; Norton, J. R.; Janak, K. E. Organometallics 2003, 22, 4084-4089. Abbreviations: dppm = bis(diphenylphosphino)methane, dppe = 1,2-bis(diphenylphosphino)ethane, dpbz = 1,2-bis(diphenylphosphino)benzene, dppp = 1,3-bis(diphenylphosphino)propane, dppb = 1,4-bis(diphenylphosphino)butane.
    • (2003) Organometallics. , vol.22 , pp. 4084-4089
    • Guan, H.1    Iimura, M.2    Magee, M.P.3    Norton, J.R.4    Janak, K.E.5
  • 50
    • 19744375863 scopus 로고    scopus 로고
    • note
    • The utility of this interplanar angle as a way of assessing the geometry of such hydride complexes has been pointed out by Lemke and Brammer, and Frost and Mebi have noted that it (the angle between the Cp ring and the Ru-P-P plane) decreases with increasing P-Ru-P bite angle within the CpRu(P-P)H series in ref 21.
  • 55
    • 19744363051 scopus 로고    scopus 로고
    • note
    • 4 after 24 h.
  • 56
    • 19744378589 scopus 로고    scopus 로고
    • note
    • 2) was converted to Cp*Ru(dppe)Cl after 24 h. As before, treatment with 1% (by weight) TEMPO (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyloxy) stopped the reaction.
  • 65
    • 19744369959 scopus 로고    scopus 로고
    • note
    • The catalytic TOF values were measured at a temperature (298 K) two degrees below that (300 K) at which the rate constants for hydride transfer were determined, and thus the agreement between the rates of the catalytic and stoichiometric reactions is even closer than the numbers in Table 2 suggest.
  • 67
    • 19744366395 scopus 로고    scopus 로고
    • note
    • Performing the same catalytic reaction with 20 mol % catalyst loading gave upfield vinyl protons at δ 3.47, 3.02, and 1.42. which were similar to those reported for other olefin complexes of CpRu cations.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.