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Volumn 36, Issue 3, 2007, Pages 362-363

Dehydrogenative condensation of (o-borylphenyl)hydrosilane with alcohols and amines

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EID: 34047271123     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.362     Document Type: Article
Times cited : (22)

References (22)
  • 1
    • 34047252983 scopus 로고    scopus 로고
    • Dehydrogenative silylation of alcohols
    • may be a more common designation in the field of organic synthesis
    • "Dehydrogenative silylation of alcohols" may be a more common designation in the field of organic synthesis.
  • 2
    • 28244473021 scopus 로고    scopus 로고
    • Some recent examples: a S. Rendler, G. Auer, M. Oestreich, Angew. Chem., Int. Ed. 2005, 44, 7620.
    • Some recent examples: a) S. Rendler, G. Auer, M. Oestreich, Angew. Chem., Int. Ed. 2005, 44, 7620.
  • 6
    • 0001214450 scopus 로고    scopus 로고
    • Selected reviews: a C. Chuit, R. J. P. Corriu, C. Reye, J. C. Young, Chem. Rev. 1993, 93, 1371.
    • Selected reviews: a) C. Chuit, R. J. P. Corriu, C. Reye, J. C. Young, Chem. Rev. 1993, 93, 1371.
  • 7
    • 0000024039 scopus 로고    scopus 로고
    • ed. by Z. Rappoport, Y. Apeloig, Wiley, Chichester, Chap. 23, p
    • b) D. Kost, I. Kalikhman, in The Chemistry of Organic Silicon Compounds, ed. by Z. Rappoport, Y. Apeloig, Wiley, Chichester, 1998, Vol. 2, Chap. 23, p. 1339.
    • (1998) The Chemistry of Organic Silicon Compounds , vol.2 , pp. 1339
    • Kost, D.1    Kalikhman, I.2
  • 8
    • 0033603612 scopus 로고    scopus 로고
    • 3-catalyzed reaction of hydrosilanes with alcohols: a) J. M. Blackwell, K. L. Foster, V. H. Beck, W. E. Piers, J. Org. Chem. 1999, 64, 4887.
    • 3-catalyzed reaction of hydrosilanes with alcohols: a) J. M. Blackwell, K. L. Foster, V. H. Beck, W. E. Piers, J. Org. Chem. 1999, 64, 4887.
  • 12
    • 34047261554 scopus 로고    scopus 로고
    • Compound la: colorless crystals (from hexane, mp 134-136°C. 1HNMR (benzene-d6, δ, 0.09 (br, 3H, 0.24 (br, 3H, 1.75-2.44 (br, 12H, 2.19 (s, 6H, 4.54 (sept, 3J, 4 Hz, 1H, 6.79 (br, 4H, 7.17 (ddd, 3J, 7 Hz, 3J, I Hz, 4J, 2 Hz, 1H, 7.24 (ddd, 3J, 7 Hz, 3J, 7 Hz, 4J, 2 Hz, 1H, 7.47 (d, 3J, 7 Hz, 1H, 7.56 (d, 3J, 7Hz, 1H, 13C{ 1H)NMR (CDCl3, δ, 2.9 (br, 21.25, 22.0-24.0 (br, 127.5-129.5 (br, 128.56, 128.97, 133.22, 134.31, 137.0-145.0 (br, 142.59, 156.7 (br, 11BNMR (THF-dg, δ) 75 (br, 29SiNMR (toluene-d8, δ, 18.0 (d of sept, 1Jsi-H, 193 Hz, 2Jsi-H, 7 Hz, MS(EI, m/z 384 (M, 34, 369 (M, Me, 99, 204 (100, IR KBr, cm
    • 2Si: C, 64.12; H, 8.84%. Found: C, 64.28; H, 9.04%.
  • 13
    • 34047265606 scopus 로고    scopus 로고
    • The high solubility of the prepared alkoxy- and aminosilanes in common organic solvents lowered their isolated yields by recrystallization or precipitation. Precipitation from CH3CN was found to suppress loss of the products to as little as possible. However, the precipitate of 7 from CH3CN was contaminated with a small amount of by-products, which are under characterization. Pure 7 was obtained by recycling preparative HPLC in 30% yield
    • 3CN was contaminated with a small amount of by-products, which are under characterization. Pure 7 was obtained by recycling preparative HPLC in 30% yield.
  • 14
    • 34047245740 scopus 로고    scopus 로고
    • Some recent examples of transition-metal-catalyzed reactions
    • Some recent examples of transition-metal-catalyzed reactions:
  • 18
    • 34047270350 scopus 로고    scopus 로고
    • w(all data) = 0.2514, GOF = 1.065, T = 173 K (CCDC No. 632074).
    • w(all data) = 0.2514, GOF = 1.065, T = 173 K (CCDC No. 632074).
  • 19
    • 0033555654 scopus 로고    scopus 로고
    • Representative examples of Si-H⋯B intramolecular interaction: a B. Wrackmeyer, O. L. Tok, Y. N. Bubnov, Angew. Chem., Int. Ed. 1999, 38, 124.
    • Representative examples of Si-H⋯B intramolecular interaction: a) B. Wrackmeyer, O. L. Tok, Y. N. Bubnov, Angew. Chem., Int. Ed. 1999, 38, 124.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.