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Volumn 11, Issue 5, 2009, Pages 1083-1086

Palladium-catalyzed sequential oxidative cyclization/coupling of 2-alkynylphenols and alkenes: A direct entry into 3-alkenylbenzofurans

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE; BENZOFURAN DERIVATIVE; PALLADIUM; PHENOL DERIVATIVE;

EID: 64349093036     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8028687     Document Type: Article
Times cited : (109)

References (34)
  • 1
    • 42049119869 scopus 로고    scopus 로고
    • Hou, X. L.; Yang, Z.; Yeung, K. S.; Wong, H. N. C. In Progress in Heterocyclic Chemistry; Gribble, G. W., Joule, J. A., Eds.; Elsevier: Oxford, 2008; 19, pp 176-207, and previous in the series. For recent work on benzofurans of pharmacological interest, see:
    • (a) Hou, X. L.; Yang, Z.; Yeung, K. S.; Wong, H. N. C. In Progress in Heterocyclic Chemistry; Gribble, G. W., Joule, J. A., Eds.; Elsevier: Oxford, 2008; Vol. 19, pp 176-207, and previous volumes in the series. For recent work on benzofurans of pharmacological interest, see:
  • 10
    • 64349114312 scopus 로고    scopus 로고
    • Compounds 2 have also been employed as starting materials in the alternative Pd-catalyzed cyclization/coupling with α-halocyclohexenones, but this procedure is limited by the availability of the required haloderivatives. See: (a) Chaplin, J. H.; Flynn, B. L. Chem. Commun. 2001, 159, 4-1595.
    • Compounds 2 have also been employed as starting materials in the alternative Pd-catalyzed cyclization/coupling with α-halocyclohexenones, but this procedure is limited by the availability of the required haloderivatives. See: (a) Chaplin, J. H.; Flynn, B. L. Chem. Commun. 2001, 159, 4-1595.
  • 13
    • 33746144885 scopus 로고    scopus 로고
    • Nakamura, M.; Ilies, L.; Otsubo, S.; Nakamura, E. Org. Lett. 2006, 8, 2803-2805. For other Pd-catalyzed cyclization/coupling sequences between 2 and organic halides or pseudohalides, see:
    • (d) Nakamura, M.; Ilies, L.; Otsubo, S.; Nakamura, E. Org. Lett. 2006, 8, 2803-2805. For other Pd-catalyzed cyclization/coupling sequences between 2 and organic halides or pseudohalides, see:
  • 16
    • 0027360182 scopus 로고    scopus 로고
    • Formation of 2-substituted tetrahydrofurans: (a) Semmelhack, M. F.; Epa, W. R. Tetrahedron Lett. 1993, 34, 7205-7208. Formation of 3-substituted indoles:
    • Formation of 2-substituted tetrahydrofurans: (a) Semmelhack, M. F.; Epa, W. R. Tetrahedron Lett. 1993, 34, 7205-7208. Formation of 3-substituted indoles:
  • 19
    • 0037423349 scopus 로고    scopus 로고
    • Formation of 3-substituted dihydrofurans
    • (d) Huang, Q. H.; Larock, R. C. J. Org. Chem. 2003, 68, 980-988. Formation of 3-substituted dihydrofurans:
    • (2003) J. Org. Chem , vol.68 , pp. 980-988
    • Huang, Q.H.1    Larock, R.C.2
  • 20
    • 25444515688 scopus 로고    scopus 로고
    • Formation of 4-substituted 2, 5-dihydro-1, 2-oxaphosphole derivatives
    • (e) Alcaide, B.; Almendros, P.; Rodriguez-Acebes, R. Chem. Eur. J. 2005, 11, 5708-5712. Formation of 4-substituted 2, 5-dihydro-1, 2-oxaphosphole derivatives:
    • (2005) Chem. Eur. J , vol.11 , pp. 5708-5712
    • Alcaide, B.1    Almendros, P.2    Rodriguez-Acebes, R.3
  • 24
    • 64349123179 scopus 로고    scopus 로고
    • See ref 6 and references cited therein
    • See ref 6 and references cited therein.
  • 32
    • 64349093541 scopus 로고    scopus 로고
    • Alternatively, excess acrylate has been reported to be involved in the regeneration of Pd (II) in some intermolecular oxidative Heck reactions. See ref 9f
    • Alternatively, excess acrylate has been reported to be involved in the regeneration of Pd (II) in some intermolecular oxidative Heck reactions. See ref 9f.
  • 34
    • 4744343636 scopus 로고    scopus 로고
    • For a recent review on oxidative palladium-catalyzed transformations, see
    • For a recent review on oxidative palladium-catalyzed transformations, see: Sigman, M. S.; Schultz, M. J. Org. Biomol. Chem. 2004, 2, 2551-2554.
    • (2004) Org. Biomol. Chem , vol.2 , pp. 2551-2554
    • Sigman, M.S.1    Schultz, M.J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.