메뉴 건너뛰기




Volumn 346, Issue 13-15, 2004, Pages 1715-1727

Cross-coupling of triallyl(aryl)silanes with aryl bromides and chlorides: An alternative convenient biaryl synthesis

Author keywords

Aryl halides; Biaryls; Cross coupling; Palladium; Terphenyls; Triallyl(aryl)silanes

Indexed keywords

ACID; ALLYL COMPOUND; ALLYL(TRIPHENYL)SILANE; BASE; BENZENE DERIVATIVE; BROMINE DERIVATIVE; CARBON; CHLORIDE; DIALLYL(DIPHENYL)SILANE; DIMETHYL SULFOXIDE; FLUORIDE; PALLADIUM COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILANE DERIVATIVE; TETRABUTYLAMMONIUM FLUORIDE; UNCLASSIFIED DRUG; WATER;

EID: 12344285900     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404188     Document Type: Article
Times cited : (97)

References (80)
  • 4
    • 0037112673 scopus 로고    scopus 로고
    • For reviews of metal-catalyzed cross-coupling reactions, see: a) Cross-Coupling Reactions: A Practical Guide: Top. Curr. Chem. 2002, 219; b) Handbook of Organopalladium Chemistry for Organic Synthesis, (Ed.: E.-i. Negishi), Wiley Interscience, New York, 2002; c) A. F. Littke, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 4176.
    • (2002) Cross-Coupling Reactions: A Practical Guide: Top. Curr. Chem. , pp. 219
  • 5
    • 0037112673 scopus 로고    scopus 로고
    • (Ed.: E.-i. Negishi), Wiley Interscience, New York
    • For reviews of metal-catalyzed cross-coupling reactions, see: a) Cross-Coupling Reactions: A Practical Guide: Top. Curr. Chem. 2002, 219; b) Handbook of Organopalladium Chemistry for Organic Synthesis, (Ed.: E.-i. Negishi), Wiley Interscience, New York, 2002; c) A. F. Littke, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 4176.
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis
  • 6
    • 0037112673 scopus 로고    scopus 로고
    • For reviews of metal-catalyzed cross-coupling reactions, see: a) Cross-Coupling Reactions: A Practical Guide: Top. Curr. Chem. 2002, 219; b) Handbook of Organopalladium Chemistry for Organic Synthesis, (Ed.: E.-i. Negishi), Wiley Interscience, New York, 2002; c) A. F. Littke, G. C. Fu, Angew. Chem. Int. Ed. 2002, 41, 4176.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4176
    • Littke, A.F.1    Fu, G.C.2
  • 17
    • 0003949622 scopus 로고
    • Butterworth & Co. Ltd. London
    • For discussions on the toxicity of triorganotin compounds, see: a) M. Pereyre, J.-P. Quintard, A. Rahm, Tin in Organic Synthesis, Butterworth & Co. Ltd. London, 1987, 6; b) I. J. Boyer, Toxicology 1989, 55, 253.
    • (1987) Tin in Organic Synthesis , pp. 6
    • Pereyre, M.1    Quintard, J.-P.2    Rahm, A.3
  • 18
    • 0024602097 scopus 로고
    • For discussions on the toxicity of triorganotin compounds, see: a) M. Pereyre, J.-P. Quintard, A. Rahm, Tin in Organic Synthesis, Butterworth & Co. Ltd. London, 1987, 6; b) I. J. Boyer, Toxicology 1989, 55, 253.
    • (1989) Toxicology , vol.55 , pp. 253
    • Boyer, I.J.1
  • 19
    • 0000390817 scopus 로고    scopus 로고
    • (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim
    • a) T. Hiyama, in: Metal-Catalyzed Cross-Coupling Reactions, (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, 421;
    • (1998) Metal-Catalyzed Cross-Coupling Reactions , pp. 421
    • Hiyama, T.1
  • 67
    • 12344337975 scopus 로고    scopus 로고
    • note
    • GC analysis did not show any peaks other than the coupled products. We do not have any convincing answer why and how such low yields of the products result. Any of the corresponding homo-coupling or protolysis products derived from aryl halides were not detected also.
  • 68
    • 12344305821 scopus 로고    scopus 로고
    • note
    • Protolysis product is obtained in the case of sterically demanding substrates due to the presence of water in the reaction mixture. Presumably the oxidative adduct preferably leads to the formation of protolysis product prior to transmetalation.
  • 75
    • 12344279613 scopus 로고    scopus 로고
    • note
    • (-) is prone to be transformed to a hexacoordinate silicate species rather than the transmetalation as evidenced previously by our group in the cross-couplings using aryltrifluorosilanes. However, this is our presumption and we do not have sufficient data to prove it.
  • 79
    • 12344321155 scopus 로고    scopus 로고
    • Aldrich Catalog No. 44,723-4
    • Aldrich Catalog No. 44,723-4.
  • 80
    • 12344283403 scopus 로고    scopus 로고
    • Aldrich Catalog No. 37,585-3
    • Aldrich Catalog No. 37,585-3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.