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Volumn 29, Issue 21, 2010, Pages 5274-5282

AlCl3-catalyzed hydrosilylation of alkynes with hydropolysilanes

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Indexed keywords


EID: 78149354825     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100376d     Document Type: Article
Times cited : (38)

References (54)
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    • Rappoport Z., Apeloig Y. Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons: New York
    • Ojima, I.; Li, Z.; Zhu, J. In The Chemistry of Organic Silicon Compounds; Rappoport, Z., Apeloig, Y., Eds.; John Wiley & Sons: New York, 1998;, Vol. 2, Pt. 2, pp 1687-1792.
    • (1998) The Chemistry of Organic Silicon Compounds , vol.2 , Issue.PART 2 , pp. 1687-1792
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  • 3
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    • Ed.; Advances in Silicon Science 1; Springer: Berlin
    • Hydrosilylation; Marciniec, B., Ed.; Advances in Silicon Science 1; Springer: Berlin, 2009.
    • (2009) Hydrosilylation
    • Marciniec, B.1
  • 5
    • 0000071378 scopus 로고
    • Radical hydrosilylation of alkynes with hydrodisilanes was reported to proceed without deterioration of the Si-Si chain. See
    • Radical hydrosilylation of alkynes with hydrodisilanes was reported to proceed without deterioration of the Si-Si chain. See: Miura, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1993, 66, 2356
    • (1993) Bull. Chem. Soc. Jpn. , vol.66 , pp. 2356
    • Miura, K.1    Oshima, K.2    Utimoto, K.3
  • 10
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    • (to Bayer A.-G.) DE 1979-2804204A1
    • Finke, U.; Moretto, H. (to Bayer A.-G.) DE 1979-2804204A1; Chem. Abstr. 1979, 91, 193413x.
    • (1979) Chem. Abstr. , vol.91
    • Finke, U.1    Moretto, H.2
  • 28
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    • Lewis acid-mediated functionalization of surface Si-H bonds of porous silicon and related materials with alkenes or alkynes has been documented. The integrity of the local structure where the reaction took place is uncertain
    • Lewis acid-mediated functionalization of surface Si-H bonds of porous silicon and related materials with alkenes or alkynes has been documented. The integrity of the local structure where the reaction took place is uncertain. Buriak, J. M.; Allen, M. J. J. Am. Chem. Soc. 1998, 120, 1339
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 1339
    • Buriak, J.M.1    Allen, M.J.2
  • 37
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    • See also
    • See also: Wagner, H.; Baumgartner, J.; Müller, T.; Marschner, C. J. Am. Chem. Soc. 2009, 131, 5022
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 5022
  • 38
    • 78149309541 scopus 로고    scopus 로고
    • note
    • GC analysis showed that traces of many other products were also formed. GC-MS suggested that one of them was a compound coming from one molecule of 1-decyne and two molecules of pentamethyldisilane. Although detailed structural characterization was not made, it can be a simple double addition product or a compound like 4 found in the phenylacetylene reaction (vide infra).
  • 39
    • 78149296422 scopus 로고    scopus 로고
    • (2-p -Anisylethyl)pentamethyldisilane was also formed in approximately 1% yield
    • (2-p -Anisylethyl)pentamethyldisilane was also formed in approximately 1% yield.
  • 40
    • 78149353434 scopus 로고    scopus 로고
    • 3 has been reported. See ref 5n
    • 3 has been reported. See ref 5n.
  • 41
    • 78149288772 scopus 로고    scopus 로고
    • Details will be reported separately
    • Details will be reported separately.
  • 43
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    • Arylsilanes.; Butterworths: London,; pp
    • Colvin, E. W. Arylsilanes. Silicon in Organic Synthesis; Butterworths: London, 1981; pp 125-133.
    • (1981) Silicon in Organic Synthesis , pp. 125-133
    • Colvin, E.W.1
  • 45
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    • note
    • (Z),α-and α,α-isomers corresponding to (Z, Z)-8fC could have also been formed as byproduct, although we did not try to search for these.
  • 46
    • 78149336392 scopus 로고    scopus 로고
    • note
    • We have encountered similar observations in transition metal-catalyzed reactions of α,ω-dihydrooligosilanes. Among α,ω- dihydrooligosilanes, 1,2-dihydrodisilanes undergo more extensive redistribution than longer chained congeners. Details will be reported separately.
  • 48
    • 78149328433 scopus 로고    scopus 로고
    • note
    • 3). GC and GC-MS analyses suggested that only the adduct coming from simple addition at the two triple bonds appeared to be formed rather selectively. However, attempted purification of the crude mixture by distillation or column chromatography after routine workup afforded unidentified compounds, which hampered further characterization of the major product. Another reaction using 2 equiv of 1a also formed the same compound as the major product.
  • 51
    • 78149305233 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum does not permit us to propose detailed structures.
  • 52
    • 0002498034 scopus 로고
    • 3Me are 218 and 215 nm, respectively. See
    • 3Me are 218 and 215 nm, respectively. See: Kumada, M.; Tamao, K. Adv. Organomet. Chem. 1968, 6, 19
    • (1968) Adv. Organomet. Chem. , vol.6 , pp. 19
    • Kumada, M.1    Tamao, K.2
  • 53
    • 78149302954 scopus 로고    scopus 로고
    • note
    • 2Si. However we are unable to exclude the possibility that the material was contaminated with other octyl-rich polymeric materials.
  • 54
    • 78149315877 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.