Abstract
The catalytic activity of a wide range of copper salts, including Cu(I) and Cu(II), has been examined in the Cu-catalyzed three-component coupling reactions of sulfonyl azides, terminal alkynes, and amines, alcohols, or water to afford N-sulfonyl amidines, imidates, and amides, respectively. Furthermore, the investigation on the ligand effect in our protocol has revealed that certain types of ligands such as tris(benzyltriazolylmethyl)amine (TBTA) exhibited notable acceleration effects on the coupling reaction. The facile and efficient methods for removing copper salts from reaction mixture were also examined.
Conference
International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-14), International Symposium on Organometallic Chemistry Directed Toward Organic Synthesis, OMCOS, Organometallic Chemistry Directed Toward Organic Synthesis, 14th, Nara, Japan, 2007-08-02–2007-08-06
References
1. A. Tuch, S. Walle. In Handbook of Combinatorial Chemistry, Vol. 2, K. C. Nicolaou, R. Hanko, W. Hartwig (Eds.), Chap. 23, Wiley-VCH, Weinheim, Germany (2002).Search in Google Scholar
2. (a) doi:10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U, A. Domling, I. Ugi. Angew. Chem., Int. Ed. 39, 3169 (2000);Search in Google Scholar
2. (b) doi:10.1002/anie.200460548, D. J. Ramon, M. Yus. Angew. Chem., Int. Ed. 44, 1602 (2005);Search in Google Scholar
2. (c) doi:10.1021/cr0505728, A. Domling. Chem. Rev. 106, 17 (2006).Search in Google Scholar
3. (a) doi:10.1021/ja0432968, I. Bae, H. Han, S. Chang. J. Am. Chem. Soc. 127, 2038 (2005);Search in Google Scholar
3. (b) doi:10.1021/ol060056j, E. J. Yoo, I. Bae, S. H. Cho, H. Han, S. Chang. Org. Lett. 8, 1347 (2006).Search in Google Scholar
4. (a) doi:10.1021/ja064788i, S. Chang, M. J. Lee, D. Y. Jung, E. J. Yoo, S. H. Cho, S. K. Han. J. Am. Chem. Soc. 128, 12366 (2006);Search in Google Scholar
4. (b) doi:10.1021/ja056399e, S. H. Cho, E. J. Yoo, I. Bae, S. Chang. J. Am. Chem. Soc. 127, 16046 (2005);Search in Google Scholar
4. (c) S. H. Cho, S. J. Hwang, S. Chang. Org. Synth. 85, 131 (2008);10.15227/orgsyn.085.0131Search in Google Scholar
4. (d) doi:10.1002/anie.200503805, M. P. Cassidy, J. Raushel, V. V. Fokin. Angew. Chem., Int. Ed. 45, 3154 (2006);Search in Google Scholar
4. (e) doi:10.1002/anie.200604358, S. H. Cho, S. Chang. Angew. Chem., Int. Ed. 46, 1897 (2007);Search in Google Scholar
4. (f) doi:10.1021/jo7016247, S. H. Kim, D. Y. Jung, S. Chang. J. Org. Chem. 72, 9769 (2007);Search in Google Scholar
4. (g) doi:10.1016/j.tetlet.2008.01.073, J. Y. Kim, S. H. Kim, S. Chang. Tetrahedron Lett. 49, 1745 (2008);Search in Google Scholar
4. (h) doi:10.1002/anie.200705940, S. H. Cho, S. Chang. Angew. Chem., Int. Ed. 47, 2836 (2008);Search in Google Scholar
4. (i) doi:10.1021/ol800049b, E. J. Yoo, S. Chang. Org. Lett. 10, 1163 (2008).Search in Google Scholar
5. (a) doi:10.1021/cr000024o, N. G. Andersen, B. A. Keay. Chem. Rev. 101, 997 (2001);Search in Google Scholar
5. (b) doi:10.1021/cr990376z, C. Kaes, A. Katz, M. W. Hosseini. Chem. Rev. 100, 3553 (2000);Search in Google Scholar
5. (c) doi:10.1021/cr040642v, H. McManus, P. J. Guiry. Chem. Rev. 104, 4151 (2004);Search in Google Scholar
5. (d) doi:10.1021/cr9902897, F. Fache, E. Schulz, M. L. Tommasino, M. Lemaire. Chem. Rev. 100, 2159 (2000).Search in Google Scholar
6. (a) doi:10.1021/ol0493094, T. R. Chan, R. Hilgraf, K. B. Sharpless, V. V. Fokin. Org. Lett. 6, 2853 (2004);Search in Google Scholar
6. (b) doi:10.1002/anie.200503936, M. Whiting, V. V. Fokin. Angew. Chem., Int. Ed. 45, 3157 (2006).Search in Google Scholar
7. (a) doi:10.1021/jo981804o, H. B. Goodbrand, N. X. Hu. J. Org. Chem. 64, 670 (1999);Search in Google Scholar
7. (b) doi:10.1016/S0040-4039(99)00903-X, A. J. Clark, R. P. Filik, G. H. Thomas. Tetrahedron Lett. 40, 4885 (1999);Search in Google Scholar
7. (c) doi:10.1021/ie0493513, T. Manifar, S. Rohani, T. P. Bender, H. B. Goodbrand, R. Gaynor, M. Saban. Ind. Eng. Chem. Res. 44, 789 (2005).Search in Google Scholar
8. doi:10.1002/anie.200604241, E. J. Yoo, M. Ahlquis, S. H. Kim, I. Bae, V. V. Fokin, K. B. Sharpless, S. Chang. Angew. Chem., Int. Ed. 46, 1730 (2007).Search in Google Scholar
9. (a) doi:10.1021/op7000172, N. Galaffu, S. P. Man, R. D. Wilkes, J. R. H. Wilson. Org. Process Res. Dev. 11, 406 (2007);Search in Google Scholar
9. (b) doi:10.1021/op049764f, C. J. Welch, J. Albaneze-Walker, W. R. Leonard, M. Biba, J. DaSilva, D. Henderson, B. Laing, D. J. Mathre, S. Spencer, X. Bu, T. Wang. Org. Process Res. Dev. 9, 198 (2005);Search in Google Scholar
9. (c) doi:10.1002/adsc.200404071, C. E. Garrett, K. Prasad. Adv. Synth. Catal. 346, 889 (2004).Search in Google Scholar
10. doi:10.1021/ie030182g, It is known that a high concentration of copper species in human body causes serious damages on liver and kidney: W. Yantasee, Y. Lin, G. E. Fryxell, K. L. Alford, B. J. Busche, C. D. Johnson. Ind. Eng. Chem. Res. 43, 2759 (2004).Search in Google Scholar
11. (a) doi:10.1021/ol7015548, S. H. Hong, R. H. Grubbs. Org. Lett. 9, 1955 (2007);Search in Google Scholar
11. (b) doi:10.1021/op0601114, F. Gallou, S. Saim, K. J. Koenig, D. Bochniak, S. T. Horhota, N. K. Yee, C. H. Senanayake. Org. Process Res. Dev. 10, 937 (2006);Search in Google Scholar
11. (c) doi:10.1016/S0040-4039(99)00726-1, H. D. Maynard, R. H. Grubbs. Tetrahedron Lett. 40, 4137 (1999);Search in Google Scholar
11. (d) doi:10.1021/ol000036w, L. A. Paquette, J. D. Schloss, I. Efremov, F. Fabris, F. Gallou, J. Mendez-Andino, J. Yang. Org. Lett. 2, 1259 (2000);Search in Google Scholar
11. (e) doi:10.1021/ol027423l, J. H. Cho, B. M. Kim, Org. Lett. 5, 531 (2003).Search in Google Scholar
12. (a) doi:10.1002/adsc.200404071, C. E. Garrett, K. Prasad. Adv. Synth. Catal. 346, 889 (2004);Search in Google Scholar
12. (b) doi:10.1021/op034072x, K. Konigsberger, G.-P. Chen, R. R. Wu, M. J. Girgis, K. Prasad, O. Repic, T. J. Blacklock. Org. Process Res. Dev. 7, 733 (2003).Search in Google Scholar
© 2013 Walter de Gruyter GmbH, Berlin/Boston