메뉴 건너뛰기




Volumn 13, Issue 3, 2011, Pages 398-401

An atom-economical access to Β-heteroarylated ketones from propargylic alcohols via tandem ruthenium/indium catalysis

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; INDIUM; KETONE; PROPANOL; PROPARGYL ALCOHOL; RUTHENIUM;

EID: 79851489230     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102706j     Document Type: Article
Times cited : (19)

References (31)
  • 9
    • 77957201035 scopus 로고    scopus 로고
    • For an example of deriving the electrophile from a styrene derivative, see
    • For an example of deriving the electrophile from a styrene derivative, see: Niggemann, M.; Bisek, N. Chem.-Eur. J. 2010, 16, 11246-11249.
    • (2010) Chem.-Eur. J. , vol.16 , pp. 11246-11249
    • Niggemann, M.1    Bisek, N.2
  • 11
    • 0000950311 scopus 로고
    • For contributions by other researchers, see
    • (b) Trost, B. M.; Livingston, R. C. J. Am Chen. Soc 1995, 117, 9586-9587. For contributions by other researchers, see:
    • (1995) J. Am. Chen. Soc. , vol.117 , pp. 9586-9587
    • Trost, B.M.1    Livingston, R.C.2
  • 13
    • 44049121779 scopus 로고
    • For isomerization to a mixture of α, β-and β, γ-enones, see: for Pd
    • (d) For isomerization to a mixture of α, β-and β, γ-enones, see: (for Pd) Lu, X.; Ji, J.; Guo, C.; Shen, W. J. Organomet. Chem. 1992, 428, 259-266.
    • (1992) J. Organomet. Chem. , vol.428 , pp. 259-266
    • Lu, X.1    Ji, J.2    Guo, C.3    Shen, W.4
  • 15
    • 79851468868 scopus 로고
    • (f) Mnn, K. Synlett 1991, 115-116.
    • (1991) Synlett , pp. 115-116
    • Mnn, K.1
  • 20
    • 0026418434 scopus 로고
    • Trost, B. M. Science 1991, 254, 1471-1477.
    • (1991) Science , vol.254 , pp. 1471-1477
    • Trost, B.M.1
  • 24
    • 79851492169 scopus 로고    scopus 로고
    • When hex-3-en-2-one, derived from alcohol 2a, was separately reacted with indole 3h in the presence of either Ru-catalyst 1, In OTf 3, or CSA, both the In-and the CSA-catalyst provided adduct 4h in similar yields and reaction time when compared to the mixture of catalysts. Ru-complex 1, however, did not provide any of adduct 4h
    • When hex-3-en-2-one, derived from alcohol 2a, was separately reacted with indole 3h in the presence of either Ru-catalyst 1, In (OTf) 3, or CSA, both the In-and the CSA-catalyst provided adduct 4h in similar yields and reaction time when compared to the mixture of catalysts. Ru-complex 1, however, did not provide any of adduct 4h.
  • 27
    • 79851486112 scopus 로고    scopus 로고
    • In the course of experiments 5 mol % of ruthenium catalyst 1 were found to provide the most reliable results for the RICA reactions
    • In the course of experiments 5 mol % of ruthenium catalyst 1 were found to provide the most reliable results for the RICA reactions.
  • 28
    • 79851489737 scopus 로고    scopus 로고
    • 1H NMR using 4-methoxyacetophenone as an internal standard
    • 1H NMR using 4-methoxyacetophenone as an internal standard.
  • 29
    • 70749115302 scopus 로고    scopus 로고
    • For an example of an asymmetric addition, see:, For nonasymmetric examples, see
    • (a) For an example of an asymmetric addition, see: Adachi, S.; Tanaka, F.; Watanabe, K.; Harada, T. Org. Lett. 2009, 11, 5206-5209. For nonasymmetric examples, see:
    • (2009) Org. Lett. , vol.11 , pp. 5206-5209
    • Adachi, S.1    Tanaka, F.2    Watanabe, K.3    Harada, T.4
  • 31
    • 0000208326 scopus 로고
    • In these reported experiments 2-methylfuran was used in large excess 4-5 equiv
    • (c) Poirier, J.-M.; Dujardin, G. Heterocycles 1987, 25, 399-407. In these reported experiments 2-methylfuran was used in large excess (4-5 equiv).
    • (1987) Heterocycles , vol.25 , pp. 399-407
    • Poirier, J.-M.1    Dujardin, G.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.