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Volumn 68, Issue 20, 2012, Pages 3885-3892

A fluorous Mukaiyama coupling reagent for a concise condensation reaction: Utility of medium-fluorous strategy

Author keywords

Condensation; Fluorous; Medium fluorous; Mukaiyama reagent; Purification

Indexed keywords

FLUORINE DERIVATIVE; REAGENT;

EID: 84859801839     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.03.034     Document Type: Article
Times cited : (18)

References (67)
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    • For examples of review: (a)
    • For examples of review: (a) Kelly, G. J.; King, F.; Kett, M. Green Chem. 2002, 4, 392-399;
    • (2002) Green Chem. , vol.4 , pp. 392-399
    • Kelly, G.J.1    King, F.2    Kett, M.3
  • 13
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    • Luorous scavengers
    • For examples: (a) Gladysz, J., Horváth, I., Curran, D. P., Eds.; Wiley-VCH: Weinheim
    • For examples: (a) Lindsley, C. W.; Leister, W. H. Fluorous scavengers In The Handbook of Fluorous Chemistry; Gladysz, J., Horváth, I., Curran, D. P., Eds.; Wiley-VCH: Weinheim, 2004; pp 236-246;
    • (2004) The Handbook of Fluorous Chemistry , pp. 236-246
    • Lindsley, C.W.1    Leister, W.H.F.2
  • 16
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    • Strategies for the recovery of fluorous catalysts and reagents: Design and evaluation
    • For examples: (a) Gladysz, J. A., Curran, D. P., Horvath, I. T., Gladysz, J., Horváth, I., Curran, D. P., Eds.; Wiley-VCH: Weinheim
    • For examples: (a) Gladysz, J. A.; Correa da Costa, R. Strategies for the recovery of fluorous catalysts and reagents: design and evaluation In The Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horvath, I. T., Gladysz, J., Horváth, I., Curran, D. P., Eds.; Wiley-VCH: Weinheim, 2004; pp 24-40;
    • (2004) The Handbook of Fluorous Chemistry , pp. 24-40
    • Gladysz, J.A.1    Correa Da Costa, R.2
  • 20
    • 4344670215 scopus 로고    scopus 로고
    • A user's guide to light fluorous chemistry
    • Gladysz, J., Horváth, I., Curran, D. P., Eds.; Wiley-VCH: Weinheim
    • (b) Curran, D. P. A user's guide to light fluorous chemistry In The Handbook of Fluorous Chemistry; Gladysz, J., Horváth, I., Curran, D. P., Eds.; Wiley-VCH: Weinheim, 2004; pp 128-155;
    • (2004) The Handbook of Fluorous Chemistry , pp. 128-155
    • Curran, D.P.1
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    • 4344670215 scopus 로고    scopus 로고
    • A user's guide to light fluorous chemistry
    • Gladysz, J., Horváth, I., Curran, D. P., Eds.; Wiley-VCH: Weinheim, light fluorous molecules typically contain 21 fluorines or fewer, and molecular weights can range from 400 to about 900 μ. They may exhibit little or even no solubility in fluorous solvent, so separations with fluorous solid phase are often the only practical methods
    • Curran, D. P. A user's guide to light fluorous chemistry In The Handbook of Fluorous Chemistry; Gladysz, J., Horváth, I., Curran, D. P., Eds.; Wiley-VCH: Weinheim, 2004; pp 128-155; light fluorous molecules typically contain 21 fluorines or fewer, and molecular weights can range from 400 to about 900 μ. They may exhibit little or even no solubility in fluorous solvent, so separations with fluorous solid phase are often the only practical methods.
    • (2004) The Handbook of Fluorous Chemistry , pp. 128-155
    • Curran, D.P.1
  • 31
    • 84859798196 scopus 로고    scopus 로고
    • note
    • There is a significant difference among isolated yields of the products due to the marked difference in crystallinity of the different reagents. Preparation of fluorous Mukaiyama reagent 3a: To a solution of 1H,1H,2H,2H-1- perfluorodecanol (15.0 g, 32.3 mmol), 2-chloropyridine (10.3 g, 77.1 mmol) in dry dichloromethane was added trifluoromethanesulfonic anhydride (10.7 g, 38.0 mmol) at 0°C and the mixture was stirred at 45°C for 24 h. Diethyl ether (100 ml) was added and the mixture was stirred for 0.5 h at room temperature. After the filtration of the crude product, the recrystallization from ethyl acetate gave 3a (19.0 g, 84%) as a white powder.
  • 32
    • 84859798195 scopus 로고    scopus 로고
    • note
    • 3S: C, 27.08, H, 1.14, N, 1.97; found: C, 26.68, H, 1.10, N, 2.11.
  • 33
    • 84859805676 scopus 로고    scopus 로고
    • note
    • 3S: C, 50.05, H, 6.77, N, 3.24; found: C, 50.02, H, 6.41, N, 3.11.
  • 34
    • 84958612634 scopus 로고    scopus 로고
    • Separations with fluorous silica gel and related materials
    • Gladysz, J., Horváth, I., Curran, D. P., Eds.; Wiley-VCH: Weinheim
    • Curran, D. P. Separations with fluorous silica gel and related materials In The Handbook of Fluorous Chemistry; Gladysz, J., Horváth, I., Curran, D. P., Eds.; Wiley-VCH: Weinheim, 2004; pp 101-127.
    • (2004) The Handbook of Fluorous Chemistry , pp. 101-127
    • Curran, D.P.1
  • 35
    • 84859802837 scopus 로고    scopus 로고
    • The fluorous TLC is TLC plate, which is coated with fluorous silica gel and commercially available from
    • The fluorous TLC is TLC plate, which is coated with fluorous silica gel and commercially available from Fluorous Technologies Inc; http://www.fluorous. com/.
  • 36
    • 84859802839 scopus 로고    scopus 로고
    • note
    • 3without 2-phenylbenzoic acid and traced for 2 h by NMR. As the result, the integration from the isopropanol stayed the same. The same experiment with the ester was also conducted.
  • 41
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    • Atomic charge is calculated by natural population analysis using NBO program (Ver. 3.1), see: (a)
    • Atomic charge is calculated by natural population analysis using NBO program (Ver. 3.1), see: (a) Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735-746;
    • (1985) J. Chem. Phys. , vol.83 , pp. 735-746
    • Reed, A.E.1    Weinstock, R.B.2    Weinhold, F.3
  • 44
    • 84859805677 scopus 로고    scopus 로고
    • note
    • FC-72 (tetradecafluorohexane) is commercially available from Aldrich; Product Number: 281042.
  • 45
    • 84859791810 scopus 로고    scopus 로고
    • note
    • HFE7100 (methoxy-nonafluorobutane) is commercially available from Aldrich; Product Number: 464309.
  • 57
    • 84859791811 scopus 로고    scopus 로고
    • PCT Int. Appl. WO2011061996
    • Seki, M. PCT Int. Appl. WO2011061996, 2011.
    • (2011)
    • Seki, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.