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Volumn 27, Issue 15, 2008, Pages 3971-3977

Suzuki coupling reactions in ether-functionalized ionic liquids: The importance of weakly interacting cations

Author keywords

[No Author keywords available]

Indexed keywords

ETHERS; IONS; LIQUIDS; ORGANIC COMPOUNDS; OXYGEN; PALLADIUM; SOLVENTS;

EID: 50549091017     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800355g     Document Type: Article
Times cited : (80)

References (52)
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    • Geldbach, T. J.; Dyson, P. J. Metal Catalysed Reactions in Ionic Liquids, Catalysis by Metal Complexes, 29; James, B. R.;, van Leeuwen P. W. M. N., Series Eds.; Springer: Dordrecht, 2005.
    • (e) Geldbach, T. J.; Dyson, P. J. Metal Catalysed Reactions in Ionic Liquids, Catalysis by Metal Complexes, Vol. 29; James, B. R.;, van Leeuwen P. W. M. N., Series Eds.; Springer: Dordrecht, 2005.
  • 6
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    • Davis, J. H., Jr Chem. Lett. 2004, 33, 1072.
    • (a) Davis, J. H., Jr Chem. Lett. 2004, 33, 1072.
  • 26
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    • The estimation of ΔHsolv using the method described in ref 10 monitors the chemical shift of the proton in the 2-position of the ring as a function of the concentration of the imidazolium salt in acetonitrile. At low concentration the ions are assumed to be completely solvated, and at high concentration it is assumed that they interact. The interactions, while being predominantly Coulombic, also involve H-bonding between the 2-proton of the imidazolium cation and the iodide anion, thus influencing the chemical shift of the 2-proton. For the ether-containing anion in 3 we also explored the interaction between the protons on the C atoms next to the O atoms of the ether groups, but no correlation was observed, so any contribution toward solvation from the ether group was ignored
    • solv using the method described in ref 10 monitors the chemical shift of the proton in the 2-position of the ring as a function of the concentration of the imidazolium salt in acetonitrile. At low concentration the ions are assumed to be completely solvated, and at high concentration it is assumed that they interact. The interactions, while being predominantly Coulombic, also involve H-bonding between the 2-proton of the imidazolium cation and the iodide anion, thus influencing the chemical shift of the 2-proton. For the ether-containing anion in 3 we also explored the interaction between the protons on the C atoms next to the O atoms of the ether groups, but no correlation was observed, so any contribution toward solvation from the ether group was ignored.
  • 27
    • 0037458833 scopus 로고    scopus 로고
    • Electrospray ionization mass spectrometry was also used to determine if 3 interacted more strongly with inorganic salts compared to 1. It is well known that ionic liquids are often observed as aggregates in ESI-MS. Halide impurities are also observed forming aggregates with the ionic liquid cations. However, in a direct comparison of 1 and 3 containing NaI no differences were observed between the aggregates observed, indicating that the magnitudes of the interaction between the two IL cations and iodide are essentially the same. See for example:(a) Dyson, P. J.; McIndoe, J. S.; Zhao, D. Chem. Commun. 2003, 508.
    • Electrospray ionization mass spectrometry was also used to determine if 3 interacted more strongly with inorganic salts compared to 1. It is well known that ionic liquids are often observed as aggregates in ESI-MS. Halide impurities are also observed forming aggregates with the ionic liquid cations. However, in a direct comparison of 1 and 3 containing NaI no differences were observed between the aggregates observed, indicating that the magnitudes of the interaction between the two IL cations and iodide are essentially the same. See for example:(a) Dyson, P. J.; McIndoe, J. S.; Zhao, D. Chem. Commun. 2003, 508.
  • 33
    • 34548686822 scopus 로고    scopus 로고
    • 3P often give high yields of C-C coupling products. However, there are several reports that show that palladium carbene complexes are poor catalysts. For example, see refs 3 and 7 and: (a) Saito, S.; Yamaguchi, H.; Muto, H.; Makino, T. Tetrahedron Lett. 2007, 48, 7498.
    • 3P often give high yields of C-C coupling products. However, there are several reports that show that palladium carbene complexes are poor catalysts. For example, see refs 3 and 7 and: (a) Saito, S.; Yamaguchi, H.; Muto, H.; Makino, T. Tetrahedron Lett. 2007, 48, 7498.
  • 34
    • 50549089802 scopus 로고    scopus 로고
    • 1H NMR spectrum following this process.
    • 1H NMR spectrum following this process.
  • 35
    • 0242543977 scopus 로고    scopus 로고
    • For X-ray structures of imidazolium chlorides: (a) Saha, S.; Hayashi, S.; Kobayashi, A.; Hamaguchi, H. Chem. Lett. 2003, 32, 740.
    • For X-ray structures of imidazolium chlorides: (a) Saha, S.; Hayashi, S.; Kobayashi, A.; Hamaguchi, H. Chem. Lett. 2003, 32, 740.
  • 38
    • 0347510881 scopus 로고    scopus 로고
    • For X-ray structures of imidazolium bromides and iodides: (a) Ozawa, R.; Hayashi, S.; Saha, S.; Kobayashi, A.; Hamaguchi, H. Chem. Lett. 2003, 32, 948.
    • For X-ray structures of imidazolium bromides and iodides: (a) Ozawa, R.; Hayashi, S.; Saha, S.; Kobayashi, A.; Hamaguchi, H. Chem. Lett. 2003, 32, 948.
  • 41
    • 26944466228 scopus 로고    scopus 로고
    • Formation of carbenes from pyridinium salts cannot be excluded; see
    • Formation of carbenes from pyridinium salts cannot be excluded; see: Albrecht, M.; Stoeckli-Evans, H. Chem. Commun. 2005, 4705.
    • (2005) Chem. Commun , pp. 4705
    • Albrecht, M.1    Stoeckli-Evans, H.2
  • 49
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    • V2.10; Bruker AXS
    • SADABS, V2.10; Bruker AXS, 2000.
    • (2000) SADABS


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.