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Volumn 352, Issue 10, 2010, Pages 1701-1710

Regio- And stereoselective intermolecular hydroalkoxylation of alkynes catalysed by cationic gold(I) complexes

Author keywords

Alkynes; Calalyst recovery; Catalysis; Enol ethers; Gold; Hydroalkoxylation

Indexed keywords


EID: 77954797371     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000094     Document Type: Article
Times cited : (63)

References (44)
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    • In the last years, intramolecular hydroalkoxylations have been incorporated into elaborated tandem processes as one of the main steps, that is, see
    • d) B. Liu, J. K. De Brabander, Org. Lett. 2006, 8, 4907. In the last years, intramolecular hydroalkoxylations have been incorporated into elaborated tandem processes as one of the main steps, that is, see
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    • [11]), where a zinc silicate is employed as heterogeneous catalyst in flow. In addition, high reaction temperatures are needed in most of the cases reported
    • [11]), where a zinc silicate is employed as heterogeneous catalyst in flow. In addition, high reaction temperatures are needed in most of the cases reported.
  • 32
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    • The well-reported alkynophilic nature of the gold centre (see, i.e. : a) D. J. Gorin, F. D. Toste, Nature 2007, 446, 395;
    • (2007) Nature , vol.446 , pp. 395
    • Gorin, D.J.1    Toste, F.D.2
  • 34
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    • together with its strong Lewis acidity makes these complexes suitable candidates for catalysts in additions to C≡C triple bonds. In fact, we have recently reported that the hydration of alkynes can be carried out at room temperature by using these gold complexes as catalysts, see
    • Angew. Chem. Int. Ed. 2006, 45, 7896) together with its strong Lewis acidity makes these complexes suitable candidates for catalysts in additions to C≡C triple bonds. In fact, we have recently reported that the hydration of alkynes can be carried out at room temperature by using these gold complexes as catalysts, see
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 7896
  • 36
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    • 1a can be purchased from Aldrich as a dimer-toluene aduct
    • N. Mezailles, L. Ricard, F. Gagosz, Org. Lett. 2005, 7, 4133; 1a can be purchased from Aldrich as a dimer-toluene aduct.
    • (2005) Org. Lett. , vol.7 , pp. 4133
    • Mezailles, N.1    Ricard, L.2    Gagosz, F.3
  • 37
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    • 2 was used as solvent since the gold complexes 1a-e can be recovered by precipitation with hexane and the reactants and products are fully soluble
    • 2 was used as solvent since the gold complexes 1a-e can be recovered by precipitation with hexane and the reactants and products are fully soluble.
  • 38
    • 0042703458 scopus 로고    scopus 로고
    • It has been reported that the E-isomer is less prone to isomerise, see: M. M. Baag, A. Kar, N. P. Argade, Tetrahedron 2003, 59, 6489.
    • (2003) Tetrahedron , vol.59 , pp. 6489
    • Baag, M.M.1    Kar, A.2    Argade, N.P.3
  • 40
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    • 4) as active catalyst for the formation of different ketals and cyclic thioketals from the corresponding alkynes and diols
    • 4) as active catalyst for the formation of different ketals and cyclic thioketals from the corresponding alkynes and diols.
    • (2008) Tetrahedron , vol.64 , pp. 7902
    • Santos, L.L.1    Ruiz, V.R.2    Sabater, M.J.3    Corma, A.4
  • 41
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    • Glycerol is a massive by-product of the biodiesel production whose market price has dramatically dropped in the last years, expected to be cheaper than other common diols such as glycol, see: A. Corma, S. Iborra, A. Velty, Chem. Rev. 2007, 107, 2411.
    • (2007) Chem. Rev. , vol.107 , pp. 2411
    • Corma, A.1    Iborra, S.2    Velty, A.3
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    • For others, see
    • For intramolecular hydroalkoxylation see: a) Ö. Aksin, N. Krause, Adv. Synth. Catal. 2008, 350, 1106. For others, see:
    • (2008) Adv. Synth. Catal. , vol.350 , pp. 1106
    • Aksin, Ö.1    Krause, N.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.