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Volumn 3, Issue 12, 2005, Pages 2228-2230

Fluorous click chemistry as a practical tagging method

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSIS; DENDRIMERS; EXTRACTION; HYDROPHOBICITY; MIXTURES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 23344445780     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b504973c     Document Type: Article
Times cited : (27)

References (35)
  • 1
    • 0002289572 scopus 로고    scopus 로고
    • ed. F. Stoddard, D. Reinhoud and M. Shibasaki, Wiley-VCH, New York
    • (a) D. P. Curran, in Stimulating Concepts in Chemistry, ed. F. Stoddard, D. Reinhoud and M. Shibasaki, Wiley-VCH, New York, 2000, p. 25;
    • (2000) Stimulating Concepts in Chemistry , pp. 25
    • Curran, D.P.1
  • 2
    • 0037071139 scopus 로고    scopus 로고
    • and the following articles in this special issue entitled "Fluorous Chemistry"
    • (b) J. A. Gladysz and D. P. Curran, Tetrahedron, 2002, 58, 3823 and the following articles in this special issue entitled "Fluorous Chemistry";
    • (2002) Tetrahedron , vol.58 , pp. 3823
    • Gladysz, J.A.1    Curran, D.P.2
  • 8
    • 2942545969 scopus 로고    scopus 로고
    • (d) W. Zhang, Chem. Rev., 2004, 104, 2531.
    • (2004) Chem. Rev. , vol.104 , pp. 2531
    • Zhang, W.1
  • 30
    • 0031725668 scopus 로고    scopus 로고
    • Reverse phase fluorous silica gel was used to separate the fluorous compounds from other organic molecules. Synthesis and application of reverse phase fluorous silica gel: S. Kainz, Z. Luo, D. P. Curran and W. Leitner, Synthesis, 1998, 1425.
    • (1998) Synthesis , pp. 1425
    • Kainz, S.1    Luo, Z.2    Curran, D.P.3    Leitner, W.4
  • 31
    • 4644326987 scopus 로고    scopus 로고
    • During the preparation of this manuscript, we became aware of an analogous study of the catalytic 1,3-dipolar cycloaddition of fluorous azides and terminal alkynes using Cu(I) catalyst: Y.-M. Wu, J. Deng, X. Fang and Q.-Y. Chen, J. Fluorine Chem., 2004, 125, 1415. Although their procedure allowed the regioselective formation of several fluorous triazoles, their yield was very poor (5%) when using conditions as described by Sharpless and applied in our report given here. Moreover, the free hydroxyl groups of their alkyne substrates need to be protected for successful reaction. The major difference between our procedure is that their fluorous azides have only one methylene spacer to insulate the electron-withdrawing effect of the perfluoroaklyl group from the azido group. Therefore we assume that efficient insulation of the perfluoroalkyl group is the reason why our azides behave similarly to the organic counterparts in click chemistry.
    • (2004) J. Fluorine Chem. , vol.125 , pp. 1415
    • Wu, Y.-M.1    Deng, J.2    Fang, X.3    Chen, Q.-Y.4
  • 34
    • 0035855262 scopus 로고    scopus 로고
    • Other fluorous cinchona alkaloids and their application: F. Fache and O. Piva, Tetrahedron Lett., 2001, 42, 5655.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 5655
    • Fache, F.1    Piva, O.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.