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ed. F. Stoddard, D. Reinhoud and M. Shibasaki, Wiley-VCH, New York
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(a) D. P. Curran, in Stimulating Concepts in Chemistry, ed. F. Stoddard, D. Reinhoud and M. Shibasaki, Wiley-VCH, New York, 2000, p. 25;
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Curran, D.P.1
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and the following articles in this special issue entitled "Fluorous Chemistry"
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(b) J. A. Gladysz and D. P. Curran, Tetrahedron, 2002, 58, 3823 and the following articles in this special issue entitled "Fluorous Chemistry";
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Gladysz, J.A.1
Curran, D.P.2
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(a) A. Studer, S. Hadida, R. Ferritto, S.-Y. Kim, P. Jeger, P. Wipf and D. P. Curran, Science, 1997, 275, 823;
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Studer, A.1
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(d) W. Zhang, Chem. Rev., 2004, 104, 2531.
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W. Chen, L. Xu, Y. Hu, Banet, A. M. Osuna and J. Xiao, Tetrahedron, 2002, 58, 3889.
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Chen, W.1
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H. C. Kolb, M. G. Finn and K. B. Sharpless, Angew. Chem., Int. Ed., 2001, 40, 2004.
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Kolb, H.C.1
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V. V. Rostovtsev, L. G. Green, V. V. Fokin and K. B. Sharpless, Angew. Chem., Int. Ed., 2002, 41, 2596.
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Rostovtsev, V.V.1
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(a) F. Fazio, M. C. Bryan, O. Blixt, J. C. Paulson and C.-H. Wong, J. Am. Chem. Soc., 2002, 124, 14397;
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(b) C. W. Torne, C. Christensen and M. Meldal, J. Org. Chem., 2002, 67, 3057;
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Torne, C.W.1
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(c) Q. Wang, T. R. Chan, R. Hilgraf, V. V. Fokin, K. B. Sharpless and M. G. Finn, J. Am. Chem. Soc., 2003, 125, 3192;
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(d) A. E. Speers, G. C. Adam and B. F. Cravatt, J. Am. Chem. Soc., 2003, 125, 4686;
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(e) L. V. Lee, M. L. Mitchell, S.-J. Huang, V. V. Fokin, K. B. Sharpless and C.H. Wong, J. Am. Chem. Soc., 2003, 125, 9588;
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Lee, L.V.1
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(g) T. S. Seo, Z, Li, H. Ruparel and J. Ju, J. Org. Chem., 2003, 68, 609;
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(h) S. Löber, P. Rodriguez-Loaiza and P. Gmeiner, Org. Lett., 2003, 5, 1753;
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(k) R. Manetsch, A. Krasinski, Z. Radic, J. Raushel, P. Taylor, K. B. Sharpless and H. C. Kolb, J. Am. Chem. Sur., 2004, 126, 12809;
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(m) B. Helms, J. L. Mynar, C. J. Hawker and J. M. J. Fréet, J. Am. Chem. Soc., 2004, 126, 15020;
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(o) J. P. Collman, N. K. Devaraj and C. E. D. Chidsey, Langmuir, 2004, 20, 1051.
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F. Szönyi, F. Guennouni and A. Cambon, J. Fluorine Chem., 1991, 55, 85.
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(a) S. Colonna, N. Gaggero, F. Montanari, G. Pozzi and S. Quici, Eur. J. Org. Chem., 2001, 181;
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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.
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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.
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