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Volumn 5, Issue 11, 2003, Pages 1895-1898

Ruthenium-catalyzed vinylsilane synthesis and cross-coupling as a selective approach to alkenes: Benzyldimethylsilyl as a robust vinylmetal functionality

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; RUTHENIUM; SILANE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYLSILANE; BENZYL DERIVATIVE; BENZYLDIMETHYLSILYL; CROSS LINKING REAGENT; PALLADIUM; SILANE DERIVATIVE;

EID: 0041851126     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034463w     Document Type: Article
Times cited : (174)

References (25)
  • 1
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    • Trost, B. M.; Machacek, M. R. Angew. Chem., Int. Ed. 2002, 41, 4693-4697. Trost, B. M.; Machacek, M.; Schnaderbeck, M. J. Org. Lett. 2000, 2, 1761-1764.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 4693-4697
    • Trost, B.M.1    Machacek, M.R.2
  • 12
    • 0001620749 scopus 로고    scopus 로고
    • Denmark, S. E.; Wehrli, D. Org. Lett. 2000, 2, 565-568. Denmark, S. E.; Wang, Z. G. Org. Lett. 2001, 3, 1073-1076.
    • (2000) Org. Lett. , vol.2 , pp. 565-568
    • Denmark, S.E.1    Wehrli, D.2
  • 13
    • 0000704507 scopus 로고    scopus 로고
    • Denmark, S. E.; Wehrli, D. Org. Lett. 2000, 2, 565-568. Denmark, S. E.; Wang, Z. G. Org. Lett. 2001, 3, 1073-1076.
    • (2001) Org. Lett. , vol.3 , pp. 1073-1076
    • Denmark, S.E.1    Wang, Z.G.2
  • 19
    • 0036003102 scopus 로고    scopus 로고
    • During the course of this work, it was reported that alkenyldimethyl-(2-thienyl)silanes offer significant acid and base stability and also function in cross-coupling reactions: Hosoi, K.; Nozaki, K.; Hiyama, T. Chem. Lett. 2002, 138-139.
    • (2002) Chem. Lett. , pp. 138-139
    • Hosoi, K.1    Nozaki, K.2    Hiyama, T.3
  • 21
    • 0141713794 scopus 로고    scopus 로고
    • note
    • Note that the BDMS does slow the rate of the alkene-alkyne coupling reaction in comparison to the TMS group. This lowers the turnover number for very complex coupling partners.
  • 22
    • 0141490512 scopus 로고    scopus 로고
    • note
    • 3·CHCl3 (2.5 0.025 equiv) was added, and the reaction was allowed to warm to room temperature. Reactions were generally complete within 4 h, whereupon the dark solution was flushed through a plug of silica with ether, concentrated in vacuo, and purified via silica chromatography.
  • 25
    • 0141602037 scopus 로고    scopus 로고
    • note
    • Fluoride-free coupling of silyl groups beating an Si-OH have been shown to be compatible with silyl ethers. See ref 4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.