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Volumn 8, Issue 14, 2006, Pages 3017-3020

Novel and selective palladium-catalyzed annulations of 2-alkynylphenols to form 2-substituted 3-halobenzo[b]furans

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EID: 33746627631     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060908f     Document Type: Article
Times cited : (97)

References (58)
  • 1
    • 84943380362 scopus 로고
    • Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford
    • (a) Donnelly, D. M. X.; Meegan, M. J. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 4, pp 657-712.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.4 , pp. 657-712
    • Donnelly, D.M.X.1    Meegan, M.J.2
  • 5
    • 0000964586 scopus 로고    scopus 로고
    • Bird, C. W., Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: London, Chapter 2.7
    • (e) Friedrichsen, W. In Comprehensive Heterocyclic Chemistry II; Bird, C. W., Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: London, 1996; Vol. 2, Chapter 2.7, pp 368-378.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.2 , pp. 368-378
    • Friedrichsen, W.1
  • 13
    • 85041692710 scopus 로고
    • For representative papers on the synthesis of benzo[b]furans via palladium-catalyzed one-pot annulations of 2-hydroxyaryl iodides with alkynes, see: (a) Arcadi, A.; Marinelli, F.; Cacchi, S. Synthesis 1986, 749.
    • (1986) Synthesis , pp. 749
    • Arcadi, A.1    Marinelli, F.2    Cacchi, S.3
  • 34
    • 0032823767 scopus 로고    scopus 로고
    • and references therein
    • For recent selected papers on palladium-free synthesis of benzo[b]-furans, see: (a) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L. Synlett 1999, 1432 and references therein.
    • (1999) Synlett , pp. 1432
    • Arcadi, A.1    Cacchi, S.2    Fabrizi, G.3    Marinelli, F.4    Moro, L.5
  • 44
    • 33746614933 scopus 로고    scopus 로고
    • note
    • 2-Alkynylphenols 1a-d were prepared from the reactions of the corresponding 2-iodophenols with terminal alkynes directly, and substrates 1e-g were obtained via three steps including O-protection, Sonogashira coupling, and O-deprotecting by known procedures, see: refs 3a and 4a.
  • 45
    • 33847087486 scopus 로고
    • It has been reported that Cu(II) as an oxidant could cleave the C-Pd σ-bond, see: (a) Bäckvall, J. E.; Nordberg, R. E. J. Am. Chem. Soc. 1980, 102, 393.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 393
    • Bäckvall, J.E.1    Nordberg, R.E.2
  • 53
    • 0035860996 scopus 로고    scopus 로고
    • For recent representative papers on protonolysis of the Pd complex to regenerate the active Pd(II) species by HCl, see: (a) Pei, T.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11290.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 11290
    • Pei, T.1    Widenhoefer, R.A.2
  • 57
    • 0030574604 scopus 로고    scopus 로고
    • and references therein
    • The other additives were used to labilize the palladium-carbon σ-bond, see: Zhu, G.; Lu, X. J Organomet. Chem. 1996, 508, 83 and references therein.
    • (1996) J Organomet. Chem. , vol.508 , pp. 83
    • Zhu, G.1    Lu, X.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.