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Volumn 12, Issue 21, 2010, Pages 4728-4731

Gold-catalyzed oxidative coupling reactions with aryltrimethylsilanes

Author keywords

[No Author keywords available]

Indexed keywords

GOLD; SILANE DERIVATIVE;

EID: 78049494200     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102194c     Document Type: Article
Times cited : (125)

References (54)
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    • For recent reviews on cross-coupling with silicon reagents, see ref 1 and
    • For recent reviews on cross-coupling with silicon reagents, see ref 1 and
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    • Selected silicon-based cross-coupling reactions
    • Selected silicon-based cross-coupling reactions
  • 20
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    • For Au-catalyzed amino- and oxyarylation of alkenes
    • For Au-catalyzed amino- and oxyarylation of alkenes
  • 29
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    • For examples of trimethylsilyl cross-coupling reactions involving an intermediate metal species, see
    • For examples of trimethylsilyl cross-coupling reactions involving an intermediate metal species, see
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    • For silicon reagents in electrophilic aromatic substitution reactions, see:;, and references therein
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    • Chan, T.H.1    Fleming, I.2
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    • 3 yields <10%
    • 3 yields <10%.
  • 35
    • 78049518255 scopus 로고    scopus 로고
    • For full details on reaction optimization and catalyst screening, see Supporting Information
    • For full details on reaction optimization and catalyst screening, see Supporting Information.
  • 36
    • 51449084463 scopus 로고    scopus 로고
    • For metal-mediated reactions of Selectfluor with arylboronic acids, see
    • For metal-mediated reactions of Selectfluor with arylboronic acids, see: Furuya, T.; Kaiser, H. M.; Ritter, T. Angew. Chem., Int. Ed. 2008, 47, 5993
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 5993
    • Furuya, T.1    Kaiser, H.M.2    Ritter, T.3
  • 39
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    • For Selectfluor-induced oxidations of electron-rich arenes, see
    • For Selectfluor-induced oxidations of electron-rich arenes, see: Zupan, M.; Iskra, J.; Stavber, S. J. Fluor. Chem. 1995, 70, 7
    • (1995) J. Fluor. Chem. , vol.70 , pp. 7
    • Zupan, M.1    Iskra, J.2    Stavber, S.3
  • 42
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    • Use of the more electron-rich silanes, such as 4-(methoxyphenyl)- trimethylsilane, yielded no product
    • Use of the more electron-rich silanes, such as 4-(methoxyphenyl)- trimethylsilane, yielded no product.
  • 43
    • 78049514644 scopus 로고    scopus 로고
    • For a recent review on the mechanism of the Wacker oxidation, see
    • For a recent review on the mechanism of the Wacker oxidation, see
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    • 78049505622 scopus 로고    scopus 로고
    • 3PAuBr readily transmetallates with boronic acids and silanols but not trimethylsilanes: See
    • 3PAuBr readily transmetallates with boronic acids and silanols but not trimethylsilanes: See
  • 48
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    • In investigations with the sila-Cope rearrangement, no transmetalation to gold(I) was observed; see
    • In investigations with the sila-Cope rearrangement, no transmetalation to gold(I) was observed; see: Horino, Y.; Luzung, M. R.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 11364
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 11364
    • Horino, Y.1    Luzung, M.R.2    Toste, F.D.3
  • 49
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    • Addition of fluoride sources, such as CsF and KF, significantly retarded the reaction. See Supporting Information for more details
    • Addition of fluoride sources, such as CsF and KF, significantly retarded the reaction. See Supporting Information for more details.
  • 52
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    • For synthetic applications of MIDA boronates, see
    • For synthetic applications of MIDA boronates, see: Gillis, E. P.; Burke, M. D. Aldrichimica Acta 2009, 42, 17
    • (2009) Aldrichimica Acta , vol.42 , pp. 17
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.