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Volumn 65, Issue 2, 2000, Pages 568-572

Effective synthesis of aryl ethers and coumaranones employing the palladium-catalyzed enyne-diyne [4 + 2] cycloaddition protocol

Author keywords

[No Author keywords available]

Indexed keywords

COUMARANONE DERIVATIVE; ETHER DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

EID: 0342632852     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991519k     Document Type: Article
Times cited : (28)

References (23)
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    • - as nucleophiles in aromatic substitution, see: (b) In The Chemistry of the Hydroxyl Group; Patai, S., Ed.; Wiley Interscience: New York, 1971; Vol. 1; p 83. For most recent works on the preparation of aryl ethers and phenols from aryl halides, see: (c) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (d) Pews, R. G.; Lysenko, Z.; Vosejpka, P. C. J. Org. Chem. 1997, 62, 8255. (e) Nayak, M. K.; Chakraborti, A. K. Tetrahedron Lett. 1997, 38, 8749.
    • (1995) Comprehensive Organic Functional Group Transformations , vol.2
    • Chiu, C.K.-F.1
  • 2
    • 1542582686 scopus 로고
    • Wiley Interscience: New York
    • - as nucleophiles in aromatic substitution, see: (b) In The Chemistry of the Hydroxyl Group; Patai, S., Ed.; Wiley Interscience: New York, 1971; Vol. 1; p 83. For most recent works on the preparation of aryl ethers and phenols from aryl halides, see: (c) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (d) Pews, R. G.; Lysenko, Z.; Vosejpka, P. C. J. Org. Chem. 1997, 62, 8255. (e) Nayak, M. K.; Chakraborti, A. K. Tetrahedron Lett. 1997, 38, 8749.
    • (1971) The Chemistry of the Hydroxyl Group , vol.1 , pp. 83
    • Patai, S.1
  • 3
    • 0000058170 scopus 로고    scopus 로고
    • - as nucleophiles in aromatic substitution, see: (b) In The Chemistry of the Hydroxyl Group; Patai, S., Ed.; Wiley Interscience: New York, 1971; Vol. 1; p 83. For most recent works on the preparation of aryl ethers and phenols from aryl halides, see: (c) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (d) Pews, R. G.; Lysenko, Z.; Vosejpka, P. C. J. Org. Chem. 1997, 62, 8255. (e) Nayak, M. K.; Chakraborti, A. K. Tetrahedron Lett. 1997, 38, 8749.
    • (1997) J. Org. Chem. , vol.62 , pp. 5413
    • Mann, G.1    Hartwig, J.F.2
  • 4
    • 0342314976 scopus 로고    scopus 로고
    • - as nucleophiles in aromatic substitution, see: (b) In The Chemistry of the Hydroxyl Group; Patai, S., Ed.; Wiley Interscience: New York, 1971; Vol. 1; p 83. For most recent works on the preparation of aryl ethers and phenols from aryl halides, see: (c) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (d) Pews, R. G.; Lysenko, Z.; Vosejpka, P. C. J. Org. Chem. 1997, 62, 8255. (e) Nayak, M. K.; Chakraborti, A. K. Tetrahedron Lett. 1997, 38, 8749.
    • (1997) J. Org. Chem. , vol.62 , pp. 8255
    • Pews, R.G.1    Lysenko, Z.2    Vosejpka, P.C.3
  • 5
    • 0030732334 scopus 로고    scopus 로고
    • - as nucleophiles in aromatic substitution, see: (b) In The Chemistry of the Hydroxyl Group; Patai, S., Ed.; Wiley Interscience: New York, 1971; Vol. 1; p 83. For most recent works on the preparation of aryl ethers and phenols from aryl halides, see: (c) Mann, G.; Hartwig, J. F. J. Org. Chem. 1997, 62, 5413. (d) Pews, R. G.; Lysenko, Z.; Vosejpka, P. C. J. Org. Chem. 1997, 62, 8255. (e) Nayak, M. K.; Chakraborti, A. K. Tetrahedron Lett. 1997, 38, 8749.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8749
    • Nayak, M.K.1    Chakraborti, A.K.2
  • 10
    • 0029860625 scopus 로고    scopus 로고
    • For the construction of alkoxybenzene derivatives via the ruthenium-catalyzed intramolecular cyclization of dienylalkynes, see: Merlic, C. A.; Pauly, M. E. J. Am. Chem. Soc. 1996, 118, 11319.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 11319
    • Merlic, C.A.1    Pauly, M.E.2
  • 11
    • 0343619896 scopus 로고    scopus 로고
    • For the synthesis of several aryl ethers as precoursors for the preparation of phenols via the palladium-catalyzed enyne-diyne [4 + 2] cycloaddition pathway, see: ref 3
    • For the synthesis of several aryl ethers as precoursors for the preparation of phenols via the palladium-catalyzed enyne-diyne [4 + 2] cycloaddition pathway, see: ref 3.
  • 12
    • 0029949373 scopus 로고    scopus 로고
    • 2a,c,3 (7) For the palladium-catalyzed [4 + 2] homo-dimerization of monosubstituted enynes, see: (a) Saito, S.; Salter, M. M.; Gevorgyan, V.; Tsuboya, N.; Tando, K.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 3970. (b) Gevorgyan, V.; Tando, K.; Uchiyama, N.; Yamamoto, Y. J. Org. Chem. 1998, 63, 7022.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 3970
    • Saito, S.1    Salter, M.M.2    Gevorgyan, V.3    Tsuboya, N.4    Tando, K.5    Yamamoto, Y.6
  • 13
    • 0000433431 scopus 로고    scopus 로고
    • 2a,c,3 (7) For the palladium-catalyzed [4 + 2] homo-dimerization of monosubstituted enynes, see: (a) Saito, S.; Salter, M. M.; Gevorgyan, V.; Tsuboya, N.; Tando, K.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 3970. (b) Gevorgyan, V.; Tando, K.; Uchiyama, N.; Yamamoto, Y. J. Org. Chem. 1998, 63, 7022.
    • (1998) J. Org. Chem. , vol.63 , pp. 7022
    • Gevorgyan, V.1    Tando, K.2    Uchiyama, N.3    Yamamoto, Y.4
  • 16
    • 0000256763 scopus 로고
    • Normally, for cleavage of the tert-butyl protection of phelols more strong acids, such as TfOH are needed; see for example: Holcombe, J. L.; Livinghouse, T. J. Org. Chem. 1986, 51, 111.
    • (1986) J. Org. Chem. , vol.51 , pp. 111
    • Holcombe, J.L.1    Livinghouse, T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.