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Volumn 8, Issue 4, 2006, Pages 793-795

Palladium-catalyzed cross-coupling reactions of heterocyclic silanolates with substituted aryl iodides and bromides

Author keywords

[No Author keywords available]

Indexed keywords

BROMINATED HYDROCARBON; IODINATED HYDROCARBON; PALLADIUM; SILANE DERIVATIVE;

EID: 33644746044     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol053165r     Document Type: Article
Times cited : (71)

References (26)
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    • (2004) Metal-Catalyzed Cross-Coupling Reactions , vol.1
    • Mitchell, T.N.1
  • 2
    • 20544450502 scopus 로고    scopus 로고
    • de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, Chapter 2
    • (a) Miyaura, N. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 1, Chapter 2.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions , vol.1
    • Miyaura, N.1
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    • (c) Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
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  • 7
    • 0003397781 scopus 로고    scopus 로고
    • de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, Chapter 4
    • (a) Denmark, S. E.; Sweis, R. F. In Metal-Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 1, Chapter 4.
    • (2004) Metal-Catalyzed Cross-Coupling Reactions , vol.1
    • Denmark, S.E.1    Sweis, R.F.2
  • 13
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    • The parent indole can be used to prepare 2- or 3-substituted indoles. Lane, B. S.; Brown, M. A.; Sames, D. J. Am. Chem. Soc. 2005, 127, 8050-8057.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 8050-8057
    • Lane, B.S.1    Brown, M.A.2    Sames, D.3
  • 20
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    • The corresponding N-Boc(2-pyrrolyl)boronic acid is a poor substrate for cross-coupling reactions as it suffers from rapid protiodeborylation and also undergoes a competing homodimerization. Johnson, C. N.; Stemp, G.; Anand, N.; Stephen, S. C.; Gallagher, T. Synlett 1998, 1025-1027.
    • (1998) Synlett , pp. 1025-1027
    • Johnson, C.N.1    Stemp, G.2    Anand, N.3    Stephen, S.C.4    Gallagher, T.5
  • 21
    • 23944506643 scopus 로고    scopus 로고
    • Cross-coupling reactions of 2-thienyl- and 2-furylboronic acids typically employ 2.0 equiv of the boronic acids. Kondolff, I.; Doucet, H.; Santelli, M. Synlett 2005, 2057-2061.
    • (2005) Synlett , pp. 2057-2061
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    • note
    • The cross-coupling of the N-Boc-(2-indolyl)- and (2-pyrrolyl)- dimethylsilanols with arylbromides was unsuccessful. Significant amounts of phenol were observed when the reactions were run at 80 °C. We believe the phenol is derived from a competing reductive elimination to form a dimethylsilyl ether that is hydrolyzed upon aqueous workup.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.