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Volumn 39, Issue 19, 1998, Pages 2937-2940

Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; THYROXINE;

EID: 0032492980     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00502-4     Document Type: Article
Times cited : (860)

References (31)
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    • Lorian, V., Ed.; Williams and Wilkins: Baltimore
    • 1) Atkinson, B. A. in Antibiotics in Laboratory Medicine; Lorian, V., Ed.; Williams and Wilkins: Baltimore, 1986, 995-1162.
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    • Atkinson, B.A.1
  • 3
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    • NAr methods
    • NAr Methods: Bois-Choussy, M.; Beugelmans, R.; Bouillon, J.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781-4784; Boger, D. L.; Borzilleri, R. M.; Nukui, S. Bioorg. Med. Chem. Lett. 1995, 5, 3091-3096; Evans, D. A.; Watson, P. S. Tetrahedron Lett. 1996, 37, 3251-3254.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 4781-4784
    • Bois-Choussy, M.1    Beugelmans, R.2    Bouillon, J.3    Zhu, J.4
  • 4
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    • NAr Methods: Bois-Choussy, M.; Beugelmans, R.; Bouillon, J.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781-4784; Boger, D. L.; Borzilleri, R. M.; Nukui, S. Bioorg. Med. Chem. Lett. 1995, 5, 3091-3096; Evans, D. A.; Watson, P. S. Tetrahedron Lett. 1996, 37, 3251-3254.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 3091-3096
    • Boger, D.L.1    Borzilleri, R.M.2    Nukui, S.3
  • 5
    • 0029964304 scopus 로고    scopus 로고
    • NAr Methods: Bois-Choussy, M.; Beugelmans, R.; Bouillon, J.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781-4784; Boger, D. L.; Borzilleri, R. M.; Nukui, S. Bioorg. Med. Chem. Lett. 1995, 5, 3091-3096; Evans, D. A.; Watson, P. S. Tetrahedron Lett. 1996, 37, 3251-3254.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 3251-3254
    • Evans, D.A.1    Watson, P.S.2
  • 18
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    • note
    • 2, resulted in the formation of significant amounts of biaryl.
  • 21
    • 33947490422 scopus 로고
    • 10) Ortho-substituted boronic acids showed a propensity to protodeborylate under the reaction conditions, leading to low conversion. (a) Kuivila, H. G.; Reuwer, J. F.; Mangravite, J. A., Jr. J. Am. Chem. Soc. 1964, 86, 2666.
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 2666
    • Kuivila, H.G.1    Reuwer, J.F.2    Mangravite J.A., Jr.3
  • 23
    • 0000706576 scopus 로고
    • 11) Phenylglycine is 60 times more racemization-prone than alanine: (a) Smith, G. G.; Sivakua, T. J. Org. Chem. 1983, 48, 627-634.
    • (1983) J. Org. Chem. , vol.48 , pp. 627-634
    • Smith, G.G.1    Sivakua, T.2
  • 25
    • 0030817242 scopus 로고    scopus 로고
    • For a recent synthesis of thyroxine see
    • 12) For a recent synthesis of thyroxine see: Salamonczyk, G. M.; Oza, V. B.; Sih, C. J. Tetrahedron Lett. 1997, 38, 6965-6968.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 6965-6968
    • Salamonczyk, G.M.1    Oza, V.B.2    Sih, C.J.3
  • 29
    • 0001307257 scopus 로고
    • For a general procedure for the synthesis of arylboronic acids see. Compound 2a is available from Aldrich Chemical Co.
    • 15) For a general procedure for the synthesis of arylboronic acids see: Brown, H. C.; Cole, T. E. Organometallics 1983, 2, 1316-1319. Compound 2a is available from Aldrich Chemical Co.
    • (1983) Organometallics , vol.2 , pp. 1316-1319
    • Brown, H.C.1    Cole, T.E.2
  • 30
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    • 16) Barton, D. H. R.; Finet, J.-P.; Khamsi, J.; Pichon, C. Tetrahedron Lett. 1986, 27, 3619-3622. For a recent report on the related arylation of amines see: Arnauld, T.; Barton, D. H. R.; Doris, E. Tetrahedron 1997, 51, 4137-4144 and references cited therein.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 3619-3622
    • Barton, D.H.R.1    Finet, J.-P.2    Khamsi, J.3    Pichon, C.4
  • 31
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    • For a recent report on the related arylation of amines see: and references cited therein
    • 16) Barton, D. H. R.; Finet, J.-P.; Khamsi, J.; Pichon, C. Tetrahedron Lett. 1986, 27, 3619-3622. For a recent report on the related arylation of amines see: Arnauld, T.; Barton, D. H. R.; Doris, E. Tetrahedron 1997, 51, 4137-4144 and references cited therein.
    • (1997) Tetrahedron , vol.51 , pp. 4137-4144
    • Arnauld, T.1    Barton, D.H.R.2    Doris, E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.