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Volumn 70, Issue 17, 2005, Pages 6964-6967

Synthesis of benzo[b]furans via CuI-catalyzed ring closure

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COPPER COMPOUNDS; KETONES; SYNTHESIS (CHEMICAL);

EID: 23644447718     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050788+     Document Type: Article
Times cited : (146)

References (44)
  • 1
    • 84943380362 scopus 로고
    • Furans and their benzo derivatives: (iii) Synthesis and applications
    • Katritzky, A. R., Ed.; Pergamon: New York
    • (a) Donelly, D. M. X.; Meegan, M. J. Furans and Their Benzo Derivatives: (iii) Synthesis and Applications. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Ed.; Pergamon: New York, 1984; Vol. 4, pp 657-712.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.4 , pp. 657-712
    • Donelly, D.M.X.1    Meegan, M.J.2
  • 3
    • 84943376011 scopus 로고
    • Synthesis of five-membered rings with one heteroatom
    • Katritzky, A. R., Ed.; Pergamon: New York
    • (c) Bird, C. W.; Cheeseman, G. W. H. Synthesis of Five-membered Rings with One Heteroatom. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Ed.; Pergamon: New York, 1984; Vol. 4, pp 89-153.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.4 , pp. 89-153
    • Bird, C.W.1    Cheeseman, G.W.H.2
  • 7
    • 0037587497 scopus 로고    scopus 로고
    • For recent, selected examples on the synthesis of benzo[b]furans, see: (a) Kraus, G. A.; Kim, I. Org. Lett. 2003, 5, 1191-1192.
    • (2003) Org. Lett. , vol.5 , pp. 1191-1192
    • Kraus, G.A.1    Kim, I.2
  • 21
    • 0029855494 scopus 로고    scopus 로고
    • Formation of dihydrobenzofuran by palladium-catalyzed ether formation was reported: (a) Palucki, M.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 10333-10334.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 10333-10334
    • Palucki, M.1    Wolfe, J.P.2    Buchwald, S.L.3
  • 25
    • 0032720602 scopus 로고    scopus 로고
    • Conversion of 1,2-dibromoarene and acetophenones to benzo[b]-furan via in situ palladium-catalyzed arylation followed by ring closure was reported: (a) Terao, Y.; Satoh, T.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1999, 72, 2345-2350.
    • (1999) Bull. Chem. Soc. Jpn. , vol.72 , pp. 2345-2350
    • Terao, Y.1    Satoh, T.2    Miura, M.3    Nomura, M.4
  • 27
    • 11444270393 scopus 로고    scopus 로고
    • (c) Recently, a Pd-catalyzed intramolecular O-arylation of enolates was disclosed: Willis, M. C.; Taylor, D.; Gillmore A. T. Org. Lett. 2004, 6, 4755-57.
    • (2004) Org. Lett. , vol.6 , pp. 4755-4757
    • Willis, M.C.1    Taylor, D.2    Gillmore, A.T.3
  • 33
    • 0041794891 scopus 로고
    • These substrates can be easily accessed via either the Friedel-Crafts acylation of the 2-halo phenyl acetyl chloride or alkylation/acylation of the 2-halo ketones/esters. See: (a) Friedel, C.; Crafts, J. M. C. R. Hebd. Seances Acad. Sci. 1877, 84, 1392, 1450.
    • (1877) C. R. Hebd. Seances Acad. Sci. , vol.84 , pp. 1392
    • Friedel, C.1    Crafts, J.M.2
  • 36
    • 33645173287 scopus 로고    scopus 로고
    • note
    • Supporting Information.
  • 37
    • 2942538871 scopus 로고    scopus 로고
    • For a recent example on a highly effective synthetic method for substituted 2-arylbenzofurans using [3,3]-sigmatropic rearrangement, see: Miyata, O.; Takeda, N.; Naito, T. Org. Lett. 2004, 6, 1761-1763.
    • (2004) Org. Lett. , vol.6 , pp. 1761-1763
    • Miyata, O.1    Takeda, N.2    Naito, T.3
  • 38
    • 0029042650 scopus 로고
    • Compound 16 was also prepared via the palladium-catalyzed annulation between iodophenol and acetelyne in 69% yield with formation of its regiosiomer in 32% yield, see: Larock, R. C.; Yum, E. K.; Doty, M. J.; Sham, K. K. C. J. Org. Chem. 1995, 60, 3270-3271.
    • (1995) J. Org. Chem. , vol.60 , pp. 3270-3271
    • Larock, R.C.1    Yum, E.K.2    Doty, M.J.3    Sham, K.K.C.4
  • 39
    • 33645189732 scopus 로고    scopus 로고
    • note
    • Compound 21 was prepared from the DIBAL-H reduction of the corresponding nitrile in toluene at ambient temperature in 90% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.