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Volumn 129, Issue 7, 2007, Pages 1987-1995

C-H activation reactions of ruthenium N-heterocyclic carbene complexes: Application in a catalytic tandem reaction involving C-C bond formation from alcohols

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; CATALYSIS; CHEMICAL BONDS; COMPLEXATION; OXIDATION; REACTION KINETICS;

EID: 33847299542     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja065790c     Document Type: Article
Times cited : (196)

References (117)
  • 43
    • 0001219836 scopus 로고    scopus 로고
    • For examples in which NHCs are substituted by phosphines, see: h
    • For examples in which NHCs are substituted by phosphines, see: (h) Simms, R. W.; Drewitt, M. J.; Baird, M. C. Organometallics 2002, 21, 2958.
    • (2002) Organometallics , vol.21 , pp. 2958
    • Simms, R.W.1    Drewitt, M.J.2    Baird, M.C.3
  • 50
    • 17444401687 scopus 로고    scopus 로고
    • For a review of tandem reactions involving more than one metal species, see
    • For a review of tandem reactions involving more than one metal species, see: Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001.
    • (2005) Chem. Rev , vol.105 , pp. 1001
    • Wasilke, J.-C.1    Obrey, S.J.2    Baker, R.T.3    Bazan, G.C.4
  • 67
    • 33646420086 scopus 로고    scopus 로고
    • Of course, electronic influence might have to be offset against changes in steric properties. See, for example: (a) Fructos, M. R, de Frémont, P, Nolan, S. P, Díaz-Requejo, M. M, Pérez, P. J. Organometallics 2006, 25, 2237
    • Of course, electronic influence might have to be offset against changes in steric properties. See, for example: (a) Fructos, M. R.; de Frémont, P.; Nolan, S. P.; Díaz-Requejo, M. M.; Pérez, P. J. Organometallics 2006, 25, 2237.
  • 69
    • 0035800494 scopus 로고    scopus 로고
    • Moreover, in a study of metathesis activity. Fürstner has noted that different NHC ligands prove optimal for different substrates: Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, R.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236.
    • Moreover, in a study of metathesis activity. Fürstner has noted that different NHC ligands prove optimal for different substrates: Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, R.; Thiel, O. R. Chem. Eur. J. 2001, 7, 3236.
  • 72
    • 9744248685 scopus 로고    scopus 로고
    • There has been a recent review of C-H activation in NHC complexes: Crudden, C. M.; Allen, D. P. Coord. Chem. Rev. 2004, 248, 2247.
    • There has been a recent review of C-H activation in NHC complexes: Crudden, C. M.; Allen, D. P. Coord. Chem. Rev. 2004, 248, 2247.
  • 94
    • 33645458949 scopus 로고    scopus 로고
    • Competitive intramolecular C-H activation and catalytic, intermolecular H/D exchange has very recently been described: Corberán, R.; Sanaú, M.; Peris, E. J. Am. Chem. Soc. 2006, 128, 3974.
    • Competitive intramolecular C-H activation and catalytic, intermolecular H/D exchange has very recently been described: Corberán, R.; Sanaú, M.; Peris, E. J. Am. Chem. Soc. 2006, 128, 3974.
  • 95
    • 33847293492 scopus 로고    scopus 로고
    • Typically, heating at 70 °C in toluene for 16-20 h was sufficient to consume Ru(PPh3)3(CO)H2, although the reaction with IMe4 required 3 days at 80 °C to give complete conversion into a mixture of 4, Ru(IMe4)2(PPh 3, CO)H2, and Ru(IMe4)3(CO)H 2
    • 2.
  • 96
    • 33847308369 scopus 로고    scopus 로고
    • 3 ligands with a cis disposition. Complete isomerization to the major isomer occurs upon standing for 16 h at room temperature.
    • 3 ligands with a cis disposition. Complete isomerization to the major isomer occurs upon standing for 16 h at room temperature.
  • 98
    • 33847291076 scopus 로고    scopus 로고
    • mesityl bonds in 1 was also investigated. See the Supporting Information for full details.
    • mesityl bonds in 1 was also investigated. See the Supporting Information for full details.
  • 101
    • 33847337155 scopus 로고    scopus 로고
    • 2: Herrmann, W. A.; Weskamp, T.; Böhm, V. P. W. Adv. Organomet. Chem. 2002, 48, 1.
    • 2: Herrmann, W. A.; Weskamp, T.; Böhm, V. P. W. Adv. Organomet. Chem. 2002, 48, 1.
  • 102
    • 33847325501 scopus 로고    scopus 로고
    • See the Supporting Information for tables of conversion data
    • See the Supporting Information for tables of conversion data.
  • 103
    • 33847328124 scopus 로고    scopus 로고
    • No difference in reactivity was seen between 9 and the dihydride precursor 8.
    • No difference in reactivity was seen between 9 and the dihydride precursor 8.
  • 104
    • 33847248178 scopus 로고    scopus 로고
    • 3 added to promote the initial C-H activation. No reduction in conversion through to product alkanes was found when catalysis was performed with alkene excluded.
    • 3 added to promote the initial C-H activation. No reduction in conversion through to product alkanes was found when catalysis was performed with alkene excluded.
  • 105
    • 33847263245 scopus 로고    scopus 로고
    • This is clear from the 2-week reaction time that is typically needed for the synthesis of 1
    • This is clear from the 2-week reaction time that is typically needed for the synthesis of 1.
  • 106
    • 33847311984 scopus 로고    scopus 로고
    • No exchange was observed without warming
    • No exchange was observed without warming.
  • 107
    • 33847256140 scopus 로고    scopus 로고
    • We have identified this compound, in the THF solution used for the reaction, via 29Si-1H correlation NMR
    • 1H correlation NMR.
  • 108
    • 33847295932 scopus 로고    scopus 로고
    • Our results cannot establish whether phosphine loss occurs only from one position within the coordination sphere
    • Our results cannot establish whether phosphine loss occurs only from one position within the coordination sphere.
  • 112
    • 0037011774 scopus 로고    scopus 로고
    • 2 is reported in: Niehues, M.; Kehr, G.; Erker, G.; Wibbeling, B.; Fröhlich, R.; Blacque, O.; Berke, H. J. Organomet. Chem. 2002, 663, 192.
    • 2 is reported in: Niehues, M.; Kehr, G.; Erker, G.; Wibbeling, B.; Fröhlich, R.; Blacque, O.; Berke, H. J. Organomet. Chem. 2002, 663, 192.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.