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Volumn 10, Issue 22, 2008, Pages 5103-5106

Carbocupration-functionalization of arynes: Rapid access to variably ortho-substituted ((E)-3-phenylprop-1-enyl)silanes

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBON; COPPER; ORGANOMETALLIC COMPOUND; SILANE DERIVATIVE;

EID: 58149202445     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8021885     Document Type: Article
Times cited : (19)

References (33)
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    • (b) Yet, L. Chem. Rev. 2003, 103, 4283-4306.
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    • Yet, L.1
  • 12
    • 0000757151 scopus 로고
    • For a recent catalytic alkynylcupration-alkynylation of symmetrical arynes, see: For an inspiring example, see: a
    • For an inspiring example, see: (a) Pansegrau, P. D.; Riecker, W. F.; Meyers, A. I. J. Am. Chem. Soc. 1988, 110, 7178-7184. For a recent catalytic alkynylcupration-alkynylation of symmetrical arynes, see:
    • (1988) J. Am. Chem. Soc , vol.110 , pp. 7178-7184
    • Pansegrau, P.D.1    Riecker, W.F.2    Meyers, A.I.3
  • 17
    • 0000611186 scopus 로고
    • For theoretical consideration of the high diastereoselectivity, see: c
    • For theoretical consideration of the high diastereoselectivity, see: (c) Fraenkel, G.; Chow, A.; Winchester, W. R. J. Am. Chem. Soc. 1990, 112, 2582-2585.
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 2582-2585
    • Fraenkel, G.1    Chow, A.2    Winchester, W.R.3
  • 18
    • 0141847248 scopus 로고    scopus 로고
    • For reviews see: a
    • For reviews see: (a) Oshima, K. Sci. Synth. 2002, 4, 713-756.
    • (2002) Sci. Synth , vol.4 , pp. 713-756
    • Oshima, K.1
  • 19
    • 33646227616 scopus 로고    scopus 로고
    • and references therein
    • (b) Whitham, G. H. Sci. Synth. 2002, 4, 633-646, and references therein.
    • (2002) Sci. Synth , vol.4 , pp. 633-646
    • Whitham, G.H.1
  • 21
    • 0037922749 scopus 로고    scopus 로고
    • Palladium-catalysed carbon-carbon cross-coupling. Overview of the Negishi protocol with Zn, Al, Zr, and related metals
    • Negishi, E.-I, Ed; John Wiley & Sons: New York
    • (a) Negishi, E.-I. Palladium-catalysed carbon-carbon cross-coupling. Overview of the Negishi protocol with Zn, Al, Zr, and related metals. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed; John Wiley & Sons: New York, 2002; Vol. 1, pp 229-247.
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , vol.1 , pp. 229-247
    • Negishi, E.-I.1
  • 22
    • 0038675899 scopus 로고    scopus 로고
    • Palladium-catalyzed cross-coupling substitution
    • Negishi, E.-I, Ed, John Wiley & Sons: New York, and references therein
    • (b) Negishi, E.-I., Dumond, Y. Palladium-catalyzed cross-coupling substitution. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; John Wiley & Sons: New York, 2002; Vol. 1, pp 767-789, and references therein.
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , vol.1 , pp. 767-789
    • Negishi, E.-I.1    Dumond, Y.2
  • 23
    • 61349128798 scopus 로고    scopus 로고
    • 2-Iodophenyl triflate 5 is converted to the corresponding aryne in the presence of 1.0 equiv of lithiated allyltrimethylsilane and 10 equiv of furan at -78 °C, affording 88% of the Diels-Alder cycloadduct.
    • 2-Iodophenyl triflate 5 is converted to the corresponding aryne in the presence of 1.0 equiv of lithiated allyltrimethylsilane and 10 equiv of furan at -78 °C, affording 88% of the Diels-Alder cycloadduct.
  • 24
    • 61349143415 scopus 로고    scopus 로고
    • When the reaction is conducted with 3.0 equiv of lithium di[3-(prop-1-enyltrimethylsilyl)]cuprate, in the absence of the extra equivalent of lithiated allyltrimethylsilane under otherwise identical conditions, 8 is generated in 39% yield.
    • When the reaction is conducted with 3.0 equiv of lithium di[3-(prop-1-enyltrimethylsilyl)]cuprate, in the absence of the extra equivalent of lithiated allyltrimethylsilane under otherwise identical conditions, 8 is generated in 39% yield.
  • 25
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    • Longer reaction times or lower temperatures have insignificant impact on yield
    • Longer reaction times or lower temperatures have insignificant impact on yield.
  • 26
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    • Acetic acid could be added with comparable results
    • Acetic acid could be added with comparable results.
  • 31
    • 0141673219 scopus 로고    scopus 로고
    • For a theoretical evaluation of relative energies of monosubstituted arynes, see
    • For a theoretical evaluation of relative energies of monosubstituted arynes, see: Maurin, P.; Ibrahim-Ouali, M.; Parrain, J.-L.; Santelli, M. THEOCHEM 2003, 637, 91-100.
    • (2003) THEOCHEM , vol.637 , pp. 91-100
    • Maurin, P.1    Ibrahim-Ouali, M.2    Parrain, J.-L.3    Santelli, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.