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Volumn 13, Issue 12, 2011, Pages 3060-3063

An efficient synthesis of imidazolinium salts using vinyl sulfonium salts

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLE DERIVATIVE; INORGANIC SALT; SULFONIUM DERIVATIVE; VINYL DERIVATIVE;

EID: 79958848103     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2009472     Document Type: Article
Times cited : (53)

References (63)
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    • Other precursors include thiones, adducts of NHCs with alcohols, or trichloromethyl groups. For examples, see
    • Other precursors include thiones, adducts of NHCs with alcohols, or trichloromethyl groups. For examples, see: Wanzlick, H. W. Angew. Chem. 1962, 74, 129-134
    • (1962) Angew. Chem. , vol.74 , pp. 129-134
    • Wanzlick, H.W.1
  • 33
    • 33745150697 scopus 로고    scopus 로고
    • For the synthesis of 5-, 6-, and 7-membered rings by the combination of formamidines with dibromo compounds or cyclic sulfonates, see
    • For the synthesis of 5-, 6-, and 7-membered rings by the combination of formamidines with dibromo compounds or cyclic sulfonates, see: Jazzar, R.; Liang, H.; Donnadieu, B.; Bertrand, G. J. Organomet. Chem. 2006, 691, 3201-3205
    • (2006) J. Organomet. Chem. , vol.691 , pp. 3201-3205
    • Jazzar, R.1    Liang, H.2    Donnadieu, B.3    Bertrand, G.4
  • 38
    • 79957872972 scopus 로고    scopus 로고
    • Eur. J. Org. Chem. 2011, early view, DOI: 10.1002/ejoc.201100337; for other related work using vinylsulfonium salts, see
    • Fritz, S. P.; Mumtaz, A.; Yar, M.; McGarrigle, E. M.; Aggarwal, V. K. Eur. J. Org. Chem. 2011, early view, DOI: 10.1002/ejoc.201100337; for other related work using vinylsulfonium salts, see
    • Fritz, S.P.1    Mumtaz, A.2    Yar, M.3    McGarrigle, E.M.4    Aggarwal, V.K.5
  • 54
    • 79958805736 scopus 로고    scopus 로고
    • Salt 1 is a commercially available stable crystalline salt and is preferred to vinylsulfonium salt 2 for ease of handling
    • Salt 1 is a commercially available stable crystalline salt and is preferred to vinylsulfonium salt 2 for ease of handling.
  • 55
    • 79955886389 scopus 로고    scopus 로고
    • For example, Grubbs has recently reported an N -aryl, N -alkyl N -heterocyclic carbene (NHC) ruthenium metathesis catalyst which was highly selective for the kinetic ethenolysis of methyl oleate at low catalyst loading (500 ppm):; J. Am. Chem. Soc. 2011, asap, DOI: 10.1021/ja200246e
    • For example, Grubbs has recently reported an N -aryl, N -alkyl N -heterocyclic carbene (NHC) ruthenium metathesis catalyst which was highly selective for the kinetic ethenolysis of methyl oleate at low catalyst loading (500 ppm): Thomas, R. M.; Keitz, B. K.; Champagne, T. M.; Grubbs, R. H. J. Am. Chem. Soc. 2011, asap, DOI: 10.1021/ja200246e.
    • Thomas, R.M.1    Keitz, B.K.2    Champagne, T.M.3    Grubbs, R.H.4
  • 56
    • 0033764021 scopus 로고    scopus 로고
    • For examples where the counterion is important in transition-metal- catalyzed reactions, see
    • For examples where the counterion is important in transition-metal- catalyzed reactions, see: Adam, W.; Roschmann, K. J.; Saha-Möller, C. R. Eur. J. Org. Chem. 2000, 3519-3521
    • (2000) Eur. J. Org. Chem. , pp. 3519-3521
    • Adam, W.1    Roschmann, K.J.2    Saha-Möller, C.R.3
  • 63
    • 79958789344 scopus 로고    scopus 로고
    • There are limits to how well elemental analysis can distinguish between the bromide and the triflate salt. While the results were entirely consistent with the triflate salts for 5a-d,f-i, contamination with up to ca. 10% bromide instead of triflate would still give satisfactory analyses. The exact limit is dependent on the molecular weight of the imidazolinium part
    • There are limits to how well elemental analysis can distinguish between the bromide and the triflate salt. While the results were entirely consistent with the triflate salts for 5a-d,f-i, contamination with up to ca. 10% bromide instead of triflate would still give satisfactory analyses. The exact limit is dependent on the molecular weight of the imidazolinium part.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.