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Volumn 128, Issue 51, 2006, Pages 16486-16487

Using triethynylphosphine ligands bearing bulky end caps to create a holey catalytic environment: Application to gold(I)-catalyzed alkyne cyclizations

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; GOLD; LIGAND; PHOSPHINE DERIVATIVE;

EID: 33845959705     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja066800c     Document Type: Article
Times cited : (136)

References (24)
  • 4
    • 33845961521 scopus 로고
    • For reactivity of alkynylphosphines, see: a
    • For reactivity of alkynylphosphines, see: (a) Borkent, G.; Drenth, W. Recueil 1970, 89, 1057-1067.
    • (1970) Recueil , vol.89 , pp. 1057-1067
    • Borkent, G.1    Drenth, W.2
  • 11
    • 33845963884 scopus 로고    scopus 로고
    • See Supporting Information for a 3D model of 1a
    • See Supporting Information for a 3D model of 1a.
  • 12
    • 29544447401 scopus 로고    scopus 로고
    • For reviews concerning gold catalysis, see: a
    • For reviews concerning gold catalysis, see: (a) Ma, S.; Yu, S.; Gu, Z. Angew. Chem., Int. Ed. 2006, 45, 200-203.
    • (2006) Angew. Chem., Int. Ed , vol.45 , pp. 200-203
    • Ma, S.1    Yu, S.2    Gu, Z.3
  • 14
    • 1842637760 scopus 로고    scopus 로고
    • For gold(I)-catalyzed cyclizations of acetylenic keto esters, see: (a) K.-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526-4527.
    • For gold(I)-catalyzed cyclizations of acetylenic keto esters, see: (a) K.-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526-4527.
  • 15
    • 7244248645 scopus 로고    scopus 로고
    • Staben, S. T.; K.-Smith, J. J.; Toste, F. D. Angew. Chem., Int. Ed. 2004, 43, 5350-5352.
    • (b) Staben, S. T.; K.-Smith, J. J.; Toste, F. D. Angew. Chem., Int. Ed. 2004, 43, 5350-5352.
  • 17
    • 3242741475 scopus 로고    scopus 로고
    • For gold(I)-catalyzed enyne cycloisomerizations, see ref 6c and; N.-Oberhuber, C, Muñoz, M. P, Buñuel, E, Nevado, C, Cádenas, D. J, Echavarren, A. M. Angew. Chem, Int. Ed. 2004, 43, 2402-2406
    • For gold(I)-catalyzed enyne cycloisomerizations, see ref 6c and; N.-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cádenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402-2406.
  • 19
    • 33845915489 scopus 로고    scopus 로고
    • 3)]/AgOTf catalyst has been reported (ref 6a), but it was much slower than the related 5-exo-dig cyclizations, requiring catalyst loading as high as 5 mol % for complete conversion (18 h).
    • 3)]/AgOTf catalyst has been reported (ref 6a), but it was much slower than the related 5-exo-dig cyclizations, requiring catalyst loading as high as 5 mol % for complete conversion (18 h).
  • 21
    • 33845929239 scopus 로고    scopus 로고
    • The donor power was estimated by DFT calculations taking the electrostatic potential minimum in the lone-pair region. Details will be reported elsewhere
    • The donor power was estimated by DFT calculations taking the electrostatic potential minimum in the lone-pair region. Details will be reported elsewhere.
  • 22
    • 33746651540 scopus 로고    scopus 로고
    • To the best of our knowledge, the gold-catalyzed 6-exo-dig cyclization of 1,7-enyne has not been reported. For examples of six-membered ring formation via gold-catalyzed 6-endo-dig cyclization of 1,5-enynes, see: Sun, J.; Conley, M. P.; Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2006, 128, 9705-9710.
    • To the best of our knowledge, the gold-catalyzed 6-exo-dig cyclization of 1,7-enyne has not been reported. For examples of six-membered ring formation via gold-catalyzed 6-endo-dig cyclization of 1,5-enynes, see: Sun, J.; Conley, M. P.; Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2006, 128, 9705-9710.
  • 23
    • 0037019690 scopus 로고    scopus 로고
    • Scattered examples of 6-exo-dig cyclizations of 1,7-enynes with non-gold-(I) catalysts have been reported. See: (a) Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294-10295.
    • Scattered examples of 6-exo-dig cyclizations of 1,7-enynes with non-gold-(I) catalysts have been reported. See: (a) Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294-10295.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.