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Volumn 10, Issue 12, 2008, Pages 2453-2456

Second-generation tags for fluorous chemistry exemplified with a new fluorous Mitsunobu reagent

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AZO COMPOUND; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FLUORINATED HYDROCARBON; PROPYLENE;

EID: 48849088330     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800750q     Document Type: Article
Times cited : (33)

References (32)
  • 1
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    • Gladysz, J. A, Curran, D. P, Horváth, I. T, Eds, Wiley-VCH: Weinheim, Germany
    • Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
    • (2004) Handbook of Fluorous Chemistry
  • 7
    • 13244274279 scopus 로고    scopus 로고
    • Gladysz, J. A, Curran, D. P, Horváth, I. T, Eds, Wiley-VCH: Weinheim, Germany
    • (a) Gladysz, J. A.; Correa de Costa, R. In The Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 24-40.
    • (2004) The Handbook of Fluorous Chemistry , pp. 24-40
    • Gladysz, J.A.1    Correa de Costa, R.2
  • 8
    • 4344670215 scopus 로고    scopus 로고
    • Gladysz, J. A, Curran, D. P, Horváth, I. T, Eds, Wiley-VCH: Weinheim, Germany
    • (b) Curran, D. P. In The Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 128-156.
    • (2004) The Handbook of Fluorous Chemistry , pp. 128-156
    • Curran, D.P.1
  • 9
    • 10044238972 scopus 로고    scopus 로고
    • Gladysz, J. A, Curran, D. P, Horváth, I. T, Eds, Wiley-VCH: Weinheim, Germany
    • Gladysz, J. A. In The Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley-VCH: Weinheim, Germany, 2004; pp 41-55.
    • (2004) The Handbook of Fluorous Chemistry , pp. 41-55
    • Gladysz, J.A.1
  • 18
    • 15544364659 scopus 로고    scopus 로고
    • Neilson, A. H, Ed, Springer-Verlag: Berlin
    • Ellis, D. A.; Moody, C. A.; Mabury, S. A. In Organofluorines; Neilson, A. H., Ed.; Springer-Verlag: Berlin, 2002; Vol. 3, pp 103-120.
    • (2002) Organofluorines , vol.3 , pp. 103-120
    • Ellis, D.A.1    Moody, C.A.2    Mabury, S.A.3
  • 19
    • 59949091731 scopus 로고    scopus 로고
    • For example, 3M reformulated Scotchgard to substitute perfluorobutane sulfonic acid (PFBS) for PFOS: http://en.wikipedia.org/wiki/ Scotchgard.
    • For example, 3M reformulated Scotchgard to substitute perfluorobutane sulfonic acid (PFBS) for PFOS: http://en.wikipedia.org/wiki/ Scotchgard.
  • 21
    • 59949092220 scopus 로고    scopus 로고
    • 3COH, CAS 2378-02-1) at a price of $3420/kg for 1 kg and $2700/kg for 10 kg.
    • 3COH, CAS 2378-02-1) at a price of $3420/kg for 1 kg and $2700/kg for 10 kg.
  • 23
    • 4143084064 scopus 로고    scopus 로고
    • For reviews on separation-friendly Mitsunobu reactions, see: a
    • For reviews on separation-friendly Mitsunobu reactions, see: (a) Dembinski, R. Eur. J. Org. Chem. 2004, 2763-2772.
    • (2004) Eur. J. Org. Chem , pp. 2763-2772
    • Dembinski, R.1
  • 25
    • 34548779745 scopus 로고    scopus 로고
    • For recent highlights on the application of fluorous Mitsunobu reactions in total synthesis, see: c
    • For recent highlights on the application of fluorous Mitsunobu reactions in total synthesis, see: (c) Dakas, P.-Y.; Barluenga, S.; Totzke, F.; Zirrgiebel, U.; Winssinger, N Angew. Chem., Int. Ed. 2007, 46, 6899-6902.
    • (2007) Angew. Chem., Int. Ed , vol.46 , pp. 6899-6902
    • Dakas, P.-Y.1    Barluenga, S.2    Totzke, F.3    Zirrgiebel, U.4    Winssinger, N.5
  • 27
    • 59949087466 scopus 로고    scopus 로고
    • The FHPLC column, FSPE cartridge, and Mitsunobu reagents are commercially available from Fluorous Technologies, Inc
    • (a) The FHPLC column, FSPE cartridge, and Mitsunobu reagents are commercially available from Fluorous Technologies, Inc.
  • 28
    • 59949096865 scopus 로고    scopus 로고
    • DPC owns an equity interest in this company
    • (b) DPC owns an equity interest in this company.
  • 32
    • 59949087718 scopus 로고    scopus 로고
    • This corresponds to about a 3% weight loading of the cartridge. We attempted a similar experiment with a 5 g cartridge (the size used for the standard Mitsunobo reagent with 26 fluorines, but significant breakthrough (∼20, of the fluorous products into the organic fraction was observed. Thus, the presence of fewer fluorines in 7p (18 fluorines) must be offset by lower loading in the FSPE
    • This corresponds to about a 3% weight loading of the cartridge. We attempted a similar experiment with a 5 g cartridge (the size used for the standard Mitsunobo reagent with 26 fluorines), but significant breakthrough (∼20%) of the fluorous products into the organic fraction was observed. Thus, the presence of fewer fluorines in 7p (18 fluorines) must be offset by lower loading in the FSPE.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.