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Volumn 10, Issue 13, 2008, Pages 2705-2708

Ruthenium catalyzed C-C bond formation via transfer hydrogenation: Branch-selective reductive coupling of allenes to paraformaldehyde and higher aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; ALKADIENE; ALLENE; CARBON; RUTHENIUM;

EID: 51649085840     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800836v     Document Type: Article
Times cited : (86)

References (47)
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    • For selected reviews on ruthenium catalyzed transfer hydrogenation, see: a
    • For selected reviews on ruthenium catalyzed transfer hydrogenation, see: (a) Zassinovich, G.; Mestroni, G.; Gladiali, S. Chem. Rev. 1992, 92, 1051.
    • (1992) Chem. Rev , vol.92 , pp. 1051
    • Zassinovich, G.1    Mestroni, G.2    Gladiali, S.3
  • 10
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    • Ruthenium complexes catalyze alkene hydroformylation. For a review, see
    • Ruthenium complexes catalyze alkene hydroformylation. For a review, see: Kalck, P.; Peres, Y.; Jenck, J. Adv. Organomet. Chem. 1991, 32, 121.
    • (1991) Adv. Organomet. Chem , vol.32 , pp. 121
    • Kalck, P.1    Peres, Y.2    Jenck, J.3
  • 11
    • 0002541696 scopus 로고
    • For ruthenium catalyzed reductive C-C bond formations beyond alkene hydroformylation, see: a
    • For ruthenium catalyzed reductive C-C bond formations beyond alkene hydroformylation, see: (a) Tsuji, Y.; Mukai, T.; Kondo, T.; Watanabe, Y. J. Organomet. Chem. 1989, 369, C51.
    • (1989) J. Organomet. Chem , vol.369
    • Tsuji, Y.1    Mukai, T.2    Kondo, T.3    Watanabe, Y.4
  • 14
    • 0035385137 scopus 로고    scopus 로고
    • For selected reviews of ruthenium catalyzed C-C coupling, see: a
    • For selected reviews of ruthenium catalyzed C-C coupling, see: (a) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067.
    • (2001) Chem. Rev , vol.101 , pp. 2067
    • Trost, B.M.1    Toste, F.D.2    Pinkerton, A.B.3
  • 17
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    • For reviews on hydrogenative C-C coupling, see: a
    • For reviews on hydrogenative C-C coupling, see: (a) Iida, H.; Krische, M. J. Top. Curr. Chem. 2007, 279, 77.
    • (2007) Top. Curr. Chem , vol.279 , pp. 77
    • Iida, H.1    Krische, M.J.2
  • 20
    • 31444453628 scopus 로고    scopus 로고
    • For recent examples, see the following. C=X vinylation: (a) Kong, J.-R.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 718.
    • For recent examples, see the following. C=X vinylation: (a) Kong, J.-R.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 718.
  • 24
    • 32644453569 scopus 로고    scopus 로고
    • Aldol and Mannich addition: (e) Jung, C.-K.; Garner, S. A.; Krische, M. J. Org. Lett. 2006, 8, 519.
    • Aldol and Mannich addition: (e) Jung, C.-K.; Garner, S. A.; Krische, M. J. Org. Lett. 2006, 8, 519.
  • 28
    • 35548993714 scopus 로고    scopus 로고
    • C=O allylation: (i) Skucas, E.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 12678.
    • C=O allylation: (i) Skucas, E.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 12678.
  • 33
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    • See the Supporting Information for detailed experimental procedures
    • See the Supporting Information for detailed experimental procedures.
  • 34
    • 59949104078 scopus 로고    scopus 로고
    • 8 as terminal reductant were conducted twice. The isolated yields and levels of deuterium incorporation for deuterio-2a and deuterio-4a were reproducible within experimental error.
    • 8 as terminal reductant were conducted twice. The isolated yields and levels of deuterium incorporation for deuterio-2a and deuterio-4a were reproducible within experimental error.
  • 35
    • 59949098709 scopus 로고    scopus 로고
    • 5)], the corresponding homoallylic alcohol and its isomers were detected. See also ref 3b.
    • 5)], the corresponding homoallylic alcohol and its isomers were detected. See also ref 3b.
  • 36
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    • For hydrometalation of allenes with Ru complexes, see: a
    • For hydrometalation of allenes with Ru complexes, see: (a) Hill, A. F.; Ho, C. T.; Wilton-Ely, J. D. E. T. Chem. Commun. 1997, 2207.
    • (1997) Chem. Commun , pp. 2207
    • Hill, A.F.1    Ho, C.T.2    Wilton-Ely, J.D.E.T.3
  • 43
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    • For Ru-catalyzed oxidative transformation of alcohols and aldehydes to esters, see: a
    • For Ru-catalyzed oxidative transformation of alcohols and aldehydes to esters, see: (a) Blum, Y.; Shvo, Y. Isr. J. Chem. 1984, 24, 144.
    • (1984) Isr. J. Chem , vol.24 , pp. 144
    • Blum, Y.1    Shvo, Y.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.