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Volumn 74, Issue 16, 2009, Pages 6398-6401

Fluorous TBAF: A convenient and selective reagent for fluoride-mediated deprotections

Author keywords

[No Author keywords available]

Indexed keywords

BIFUNCTIONAL MOLECULES; CHEMICAL EQUATIONS; CHROMATOGRAPHIC SEPARATIONS; CRUDE MIXTURES; FLUOROUS; HIGH PURITY; PROTECTING GROUP; SOLID-PHASE EXTRACTION;

EID: 70349118104     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901245m     Document Type: Article
Times cited : (10)

References (39)
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    • (a) Zhang, W. Tetrahedron 2003, 59, 4475-4489.
    • (2003) Tetrahedron , vol.59 , pp. 4475-4489
    • Zhang, W.1
  • 5
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    • Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley- VCH: Weinheim, Germany
    • (b) Handbook of Fluorous Chemistry; Gladysz, J. A., Curran, D. P., Horváth, I. T., Eds.; Wiley- VCH: Weinheim, Germany, 2004.
    • (2004) Handbook of Fluorous Chemistry
  • 6
    • 2942545969 scopus 로고    scopus 로고
    • (c) Zhang, W. Chem. Rev. 2004, 104, 2531-2556.
    • (2004) Chem. Rev. , vol.104 , pp. 2531-2556
    • Zhang, W.1
  • 8
    • 65249160131 scopus 로고    scopus 로고
    • (e) Zhang, W. Chem. Rev. 2009, 109, 749-795.
    • (2009) Chem. Rev. , vol.109 , pp. 749-795
    • Zhang, W.1
  • 16
    • 0344010055 scopus 로고    scopus 로고
    • For the synthesis of similar fluorous TBAI analogues, see
    • For the synthesis of similar fluorous TBAI analogues, see: Gupta, O. D.; Armstrong, P. D.; Shreeve, J. M. Tetrahedron Lett. 2003, 44, 9367-9370.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 9367-9370
    • Gupta, O.D.1    Armstrong, P.D.2    Shreeve, J.M.3
  • 17
    • 70349107474 scopus 로고    scopus 로고
    • note
    • The crude mixture was eluted through fluorous silica gel with 67% aqueous MeOH to afford pure BnOH, whereas all fluorous species remained adsorbed onto the solid support. The low solubility of the TES-F byproduct precluded its elution in the fluorophobic fraction.
  • 32
  • 33
  • 34
    • 64249101450 scopus 로고    scopus 로고
    • For selected examples, see: (c)
    • For selected examples, see: (c) Shah, S. T. A.; Singh, S.; Guiry, P. J. J. Org. Chem. 2009, 74, 2179-2182.
    • (2009) J. Org. Chem. , vol.74 , pp. 2179-2182
    • Shah, S.T.A.1    Singh, S.2    Guiry, P.J.3
  • 38
    • 70349146082 scopus 로고    scopus 로고
    • note
    • Both the TMSE and Teoc groups in compounds 24 and 26 (Table 3, entries 4 and 5) were stable even in the presence of a larger excess of FTBAF. In contrast, 2 equiv of nonfluorous TBAF fully deprotected both substrates.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.