Direct guanidinylation of aryl and heteroaryl halides via copper-catalyzed cross-coupling reaction

Journal of Organic Chemistry

Volumn 77, Issue 1, 2012, Pages 417-423

  Hammoud, Hassan ^a   Schmitt, Martine ^a   Bihel, Frédéric ^a   Antheaume, Cyril ^a   Bourguignon, Jean Jacques ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS COUPLING REACTIONS; GOOD YIELD; P-METHOXYBENZYL; ULLMANN REACTION;

CHEMISTRY; ORGANIC COMPOUNDS;

CHEMICAL REACTIONS;

4 METHOXYBENZYL GUANIDINE; AMIDE; ANILINE; CARBAMIC ACID DERIVATIVE; COPPER; GUANIDINE; GUANIDINE DERIVATIVE; HALIDE; PALLADIUM; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; NUCLEOPHILICITY; ULLMANN REACTION;

CATALYSIS; COPPER; CROSS-LINKING REAGENTS; GUANIDINES; HYDROCARBONS, HALOGENATED; MOLECULAR STRUCTURE;

EID: 84855544517     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202018w     Document Type: Article

References (37)

1. Torborg, C.; Beller, M. Adv. Synth. Catal. 2009, 351, 3027
2. Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338
3. Carey, J. S.; Laffan, C.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337
4. King, A. O.; Yasuda, N. Top. Organomet. Chem. 2004, 6, 205
5. Baeza, A.; Burgos, C.; Builla, J. A.; Vaquero, J. J. Tetrahedron Lett. 2007, 48, 2597
6. Bauer, D.; Whittington, D. A.; Coxon, A.; Bready, J.; Harriman, S. P.; Patel, V. F.; Polverino, A.; Harmange, J. C. Bioorg. Med. Chem. Lett. 2008, 18, 4844
7. De Deyn, P. P.; Marescau, B.; Stalon, V.; Qureshi, I. A. Guanidino Compounds in Biology and Medicine; John Libbey & Co. Ltd.: London, 1992.
8. Olivier, D. W.; Dormehl, I. C.; Wikberg, J.; Dambrova, M. Med. Chem. Res. 2005, 13, 427
9. Rodriguez, F.; Rozas, I.; Ortega, J. E.; Meana, J. J.; Callado, L. F. J. Med. Chem. 2009, 52, 601
10. Joossens, J.; Ali, O. M.; Sayed, I.; Surpateanu, G.; Veken, P. V.; Augustyns, K. J. Med. Chem. 2007, 50, 6638
11. Bahekar, R. H.; Jain, M. R.; Goel, A.; Patel, D. N.; Jadav, P. A.; Patel, P. R. Bioorg. Med. Chem. 2007, 15, 3248
12. Powel, D. A.; Ramsden, P. D.; Batey, R. A. J. Org. Chem. 2003, 68, 2300
13. Katrizky, A. R.; Khashab, N. M.; Bobrov, S. Helv. Chim. Acta 2005, 88, 1664
14. Yang, X.; Liu, H.; Fu, H.; Qiao, R.; Jiang, Y.; Zhao, Y. Synlett 2010, 1, 101
15. Salva, M. C.; Nguyen, B. L.; Cuevas, J.; Pennypacker, K. R.; Antilla, J. C. Org. Lett. 2010, 12, 1316
16. Evindar, G.; Batey, R. A. Org. Lett. 2003, 5, 133
17. Deng, X.; McAllister, H.; Mani, N. S. J. Org. Chem. 2009, 74, 5742
18. Fors, B. P.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 15914
19. Fors, B. P.; Krattiger, P.; Strieter, E.; Buchwald, S. L. Org. Lett.. 2008, 10, 3505
20. Sheng, Q.; Hartwig, J. F. Org. Lett. 2008, 10, 4109
21. Vo, G. D.; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, 11049
22. Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046
23. Fanta, P. E. Synthesis 1974, 1, 9
24. Wu, Q.; Wang, L. Synthesis 2008, 2007
25. Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581
26. Wolf, C.; Liu, S.; Mei, X.; August, A. T.; Casimir, M. D. J. Org. Chem. 2006, 71, 3270
27. Monnier, F.; Taillefer, M. Angew. Chem., Int. Ed. 2009, 48, 6954
28. Evano, G.; Toumib, M.; Costea, A. Chem. Commun. 2009, 4166
29. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421
30. Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727
31. Gavade, S. N.; Balaskar, R. S.; Mane, M. S.; Pabrekar, P. N.; Shingare, M. S.; Mane, D. V. Chin. Chem. Lett. 2011, 22, 292
32. Yadav, L. D. S.; Yadav, B. S.; Rai, V. K. Synthesis 2006, 11, 1868
33. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421
34. Guery, S.; Schmitt, M.; Bourguignon, J. J. Syntlett 2002, 12, 2003
35. Miel, H.; Rault, S. Tetrahedron Lett. 1998, 39, 1565
36. Feichtinger, K.; Sings, H. L.; Baker, T. J.; Matthews, K.; Goodman, M. J. Org. Chem. 1998, 63, 8432
37. Geoffrey, C.; Brian, F.; Alan, H.; John, M. T.; Mark, M.; Mahmoud, A.; Alan, K.; Justice, T.; Roger, W. J. Med. Chem. 2009, 52, 3457