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Volumn 73, Issue 2, 2008, Pages 495-501

Direct one-pot synthesis of phenanthrenes via Suzuki-Miyaura coupling/aldol condensation cascade reaction

Author keywords

[No Author keywords available]

Indexed keywords

ALDOL CONDENSATION; SUZUKI-MIYAURA COUPLING;

EID: 40949083397     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702001n     Document Type: Article
Times cited : (57)

References (67)
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    • For recent reviews of microwave heating technology, see: a
    • For recent reviews of microwave heating technology, see: (a) Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250-6284.
    • (2004) Angew. Chem., Int. Ed , vol.43 , pp. 6250-6284
    • Kappe, C.O.1
  • 54
    • 41149170193 scopus 로고    scopus 로고
    • For preparation of 1a-f, 1k, and 2b, see Supporting Information.
    • For preparation of 1a-f, 1k, and 2b, see Supporting Information.
  • 55
    • 32644441797 scopus 로고    scopus 로고
    • For a microwave-enhanced Suzuki-Miyaura reaction of 2-formylphenylboronic acid, see: Beryozkina, T.; Appukkuttan, P.; Mont, N.; Van der Eycken, E. Org. Lett. 2006, 8, 487-490.
    • For a microwave-enhanced Suzuki-Miyaura reaction of 2-formylphenylboronic acid, see: Beryozkina, T.; Appukkuttan, P.; Mont, N.; Van der Eycken, E. Org. Lett. 2006, 8, 487-490.
  • 56
    • 0000851696 scopus 로고
    • Trost, B. M, Ed, Pergamon Press: Oxford
    • (a) Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 2, p 133.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 133
    • Heathcock, C.H.1
  • 57
    • 41149093488 scopus 로고
    • For preparation of a phenanthrene ring using aldol condensation of methyl 2′-formylbiphenyl-2-acetate, see
    • (b) For preparation of a phenanthrene ring using aldol condensation of methyl 2′-formylbiphenyl-2-acetate, see: Saha, M.; Das, T. K.; Das, A.; Ghosh, N. R. Synth. Commun. 1990, 20, 137-151.
    • (1990) Synth. Commun , vol.20 , pp. 137-151
    • Saha, M.1    Das, T.K.2    Das, A.3    Ghosh, N.R.4
  • 58
    • 0033564994 scopus 로고    scopus 로고
    • On the basis of GC/MS analysis, we observed that dehalogenated product was obtained as a major side product (∼5%) and that intramolecular cyclization product 9 was not detected under these conditions, see: Yang, B. H.; Buchwald, S. L. Org. Lett. 1999, 1, 35-38. (Chemical Equation Presented)
    • On the basis of GC/MS analysis, we observed that dehalogenated product was obtained as a major side product (∼5%) and that intramolecular cyclization product 9 was not detected under these conditions, see: Yang, B. H.; Buchwald, S. L. Org. Lett. 1999, 1, 35-38. (Chemical Equation Presented)
  • 59
    • 41149129689 scopus 로고    scopus 로고
    • In cases of aryl bromides such as 2-bromobenzyl methyl ether and N-(2-bromobenzyl)acetamide, we failed to obtain the corresponding phenanthrenes.
    • In cases of aryl bromides such as 2-bromobenzyl methyl ether and N-(2-bromobenzyl)acetamide, we failed to obtain the corresponding phenanthrenes.
  • 64
    • 27644475970 scopus 로고    scopus 로고
    • Wiley-VCH: Weinheim, Germany
    • (b) Hall, D. G. Boronic Acids; Wiley-VCH: Weinheim, Germany, 2005.
    • (2005) Boronic Acids
    • Hall, D.G.1
  • 66
    • 41149114646 scopus 로고    scopus 로고
    • We have evaluated reaction conditions using a variety of palladium sources (Pd(PPh3)4, Pd(OAc)2, and PdCl 2) and ligands DavePhos, XPhos, and SPhos
    • 2) and ligands (DavePhos, XPhos, and SPhos).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.