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Volumn 70, Issue 2, 2005, Pages 556-561

Regioselective hydrosilylations of propiolate esters with tris(trimethylsilyl)silane

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL METHODS; SILANES; SILICON; SUBSTRATES;

EID: 12344318987     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048371b     Document Type: Article
Times cited : (50)

References (41)
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    • (b) Hiyama, T.; Kusumoto, T. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 8, p 763.
    • (1991) Comprehensive Organic Synthesis , vol.8 , pp. 763
    • Hiyama, T.1    Kusumoto, T.2
  • 9
    • 0000975316 scopus 로고    scopus 로고
    • Tris(trimethylsilyl)-silane in Organic Synthesis
    • Rappoport, S., Apeloig, Y., Eds.; Wiley: New York
    • (c) Chatgilialoglu, C.; Ferreri, C.; Gimisis, T. Tris(trimethylsilyl)- silane in Organic Synthesis. In The Chemistry of Organic Silicon Compounds; Rappoport, S., Apeloig, Y., Eds.; Wiley: New York, 1998; Vol. 2, p 1539.
    • (1998) The Chemistry of Organic Silicon Compounds , vol.2 , pp. 1539
    • Chatgilialoglu, C.1    Ferreri, C.2    Gimisis, T.3
  • 15
    • 0000390817 scopus 로고    scopus 로고
    • Organosilicon Compounds in Cross-Coupling Reactions
    • Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany
    • (b) Hiyama, T.; Hatanaka, Y. Organosilicon Compounds in Cross-Coupling Reactions. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
    • (1998) Metal-catalyzed Cross-coupling Reactions
    • Hiyama, T.1    Hatanaka, Y.2
  • 19
    • 0002331417 scopus 로고    scopus 로고
    • Renaud, P., Sibi, M. P., Eds; Wiley-VCH: Weinheim, Germany
    • (b) Chatgilialoglu, C. Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, p 28.
    • (2001) Radicals in Organic Synthesis , vol.1 , pp. 28
    • Chatgilialoglu, C.1
  • 24
    • 12344278418 scopus 로고    scopus 로고
    • note
    • 1H NMR.
  • 25
    • 12344278040 scopus 로고    scopus 로고
    • note
    • 2 under an oxygen atmosphere gave 4a in only 10% yield, with an unidentified mixture.
  • 26
    • 0001298427 scopus 로고
    • The reaction of 1a and 2b with indium catalyst undergoes cyclotrimerization instead of hydrosilylation. Tanke, R. S.; Crabtree, R. H. J. Am. Chem. Soc. 1990, 112, 7984.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 7984
    • Tanke, R.S.1    Crabtree, R.H.2
  • 32
    • 12344322959 scopus 로고    scopus 로고
    • note
    • 343 relative to reactants 2a and oxygen is 39.2 kcal/mol.
  • 34
    • 12344286389 scopus 로고    scopus 로고
    • note
    • 3 and the σ-complex Y is stable (ΔG = -17.7 kcal/mol).
  • 36
    • 12344315328 scopus 로고    scopus 로고
    • note
    • 2.
  • 38
    • 12344255279 scopus 로고    scopus 로고
    • note
    • 1H NMR) proceeded in 37% (for 1a) and 47% (for 1c) conversion to give 3a and 3c, respectively. Therefore, the radical and ionic processes compete under these reaction conditions. Some inconsistency in isolated yields may arise from the possibilities that the reaction completed after treatment with water or the °-addition reaction is accelerated by weak Lewis acids or catalytic Lewis acid.
  • 39
    • 12344258209 scopus 로고    scopus 로고
    • note
    • 2 attack.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.