Regioselective copper-catalyzed C-N and C-S bond formation using amines, thiols and halobenzoic acids

Synthesis

Volumn , Issue 22, 2007, Pages 3519-3527

  Liu, Shuanglong ^a   Pestano, John Paul C ^a   Wolf, Christian ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

Amines; Carbon heteroatom bond formation; Halobenzoic acids; Thiols

Indexed keywords

CARBON-HETEROATOM BOND FORMATION; ETHYLENE GLYCOL DIETHYL ETHER; HALOBENZOIC ACIDS; REGIOSELECTIVE; THIOLS;

ADDITIVES; AMINES; CHEMICAL BONDS; ETHERS; ETHYLENE GLYCOL; REGIOSELECTIVITY;

CARBOXYLIC ACIDS;

2 (2,6 DIMETHYLPHENYLTHIO)BENZOIC ACID; 2 (4 FLUOROPHENYLTHIO)BENZOIC ACID; 2 (4 METHOXYPHENYLTHIO)BENZOIC ACID; 2 (HEXYLTHIO)BENZOIC ACID; 2 (PHENETHYLTHIO)BENZOIC ACID; 2 (PHENYLTHIO) 4 FLUOROBENZOIC ACID; 2 (PHENYLTHIO) 5 METHOXYBENZOIC ACID; 2 (PHENYLTHIO) 5 NITROBENZOIC ACID; 2 (PHENYLTHIO)BENZOIC ACID; 2 BROMOBENZOIC ACID; 2 CHLOROBENZOIC ACID; 3,4 DIMETHOXY N PHENETHYLANTHRANILIC ACID; 4 CHLORO N PHENETHYLANTHRANILIC ACID; 4 FLUORO N BENZYLANTHRANILIC ACID; 4 NITRO N PHENETHYLANTHRANILIC ACID; 5 BROMO 2 (PHENYLTHIO)BENZOIC ACID; 5 BROMO N PHENETHYLANTHRANILIC ACID; 5 CARBOXY N BENZYLANTHRANILIC ACID; 5 CHLORO N PHENETHYLANTHRANILIC ACID; 5 METHOXY N BENZYLANTHRANILIC ACID; 5 NITRO N BENZYLANTHRANILIC ACID; AMINE; ANTHRANILIC ACID DERIVATIVE; BENZOIC ACID DERIVATIVE; COPPER; ENFENAMIC ACID; N BENZYLANTHRANILIC ACID; N CYLOHEXYLANTHRANILIC ACID; N PENTYLANTHRANILIC ACID; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 36749077543     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990875     Document Type: Article

References (45)

1. (a) Ottolia, M.; Toro, L. Biophys. J. 1994, 67, 2272.
2. (b) Farrugia, G.; Nitecki, S.; Harty, G. J.; Camilleri, M.; Szurszewski, J. H. Gut 1998, 42, 258.
3. (a) Green, N. S.; Palaninathan, S. K.; Sacchettini, J. C.; Kelly, J. W. J. Am. Chem. Soc. 2003, 125, 13404.
4. (b) Klabunde, T.; Petrassi, H. M.; Oza, V. B.; Raman, P.; Kelly, J. W.; Saccettini, J. C. Nat. Struct. Biol. 2000, 7, 312.
5. (c) Oza, V. B.; Smith, C.; Raman, B.; Koepf, E. K.; Lashuel, H. A.; Petrassi, H. M.; Chiang, K. P.; Powers, E. T.; Sachettinni, J.; Kelly, J. W. J. Med. Chem. 2002, 45, 321.
6. (a) Inai, Y.; Kurokawa, Y.; Ida, A.; Hirabayashi, T. Bull. Chem. Soc. Jpn. 1999, 72, 55.
7. (b) Ramesh, K.; Balaram, P. Bioorg. Med. Chem. 1999, 7, 105.
8. (c) Abele, S.; Seebach, D. Eur. J Org. Chem. 2000, 1.
9. (d) Inai, Y.; Tagawa, K.; Takasu, A.; Hirabayashi, T.; Oshikawa, T.; Yamashita, M. J. Am. Chem. Soc. 2000, 122, 11731.
10. (e) Inai, Y.; Ousaka, N.; Okabe, T. J. Am. Chem. Soc. 2003, 125, 8151.
11. Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382.
12. (a) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
13. (b) Wolf, C.; Mei, X. J. Am. Chem. Soc. 2003, 125, 10651.
14. (c) Docampo Palacios, M. L.; Pello Comdom, R. F. Synth. Commun. 2003, 33, 1771.
15. (d) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428.
16. (e) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
17. (f) Dokorou, V.; Kovala-Demertzi, D.; Jasinski, J. P.; Galani, A.; Demertzis, M. A. Helv. Chim. Acta 2004, 87, 1940.
18. (g) Mei, X.; Wolf, C. Chem. Commun. 2004, 2078.
19. (h) Mei, X.; Wolf, C. J. Am. Chem. Soc. 2004, 126, 14736.
20. (i) Mei, X.; Wolf, C. J. Org. Chem. 2005, 70, 2299.
21. Stauffer, S. R.; Steinbeiser, M. A. Tetrahedron Lett. 2005, 46, 2571.
22. Csuk, R.; Barthel, A.; Raschke, C. Tetrahedron 2004, 60, 5737.
23. (a) Beard, R. L.; Colon, D. F.; Song, T. K.; Davies, P. J. A.; Kochhar, D. M.; Chandraratna, R. A. S. J. Med. Chem. 1996, 39, 3556.
24. (b) Potin, D.; Parnet, V.; Teulon, J.-M.; Camborde, F.; Caussade, F.; Meignen, J.; Provost, D.; Cloarec, A. Bioorg. Med. Chem. Lett. 2000, 10, 805.
25. (a) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2002, 4, 3517.
26. (b) Fernandez-Rodriguez, M. A.; Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 2180.
27. Kalinin, A. V.; Bower, J. F.; Riebel, P.; Snieckus, V. J. Org. Chem. 1999, 64, 2986.
28. Geertsma, E. M.; Hoen, R.; Meetsma, A.; Feringa, B. L. Eur. J. Org. Chem. 2006, 3596.
29. (a) Mei, X.; August, A. T.; Wolf, C. J. Org. Chem. 2006, 71, 142.
30. (b) Wolf, C.; Liu, S.; Mei, X.; August, A. T.; Casimir, M. D. J. Org. Chem. 2006, 71, 3270.
31. (a) Maradolla, M. B.; Amaravathi, M.; Kumar, V. N.; Mouli, G. V. P. C. J. Mol. Catal. A: Chem. 2007, 266, 47.
32. (b) Rodriguez-Dominguez, J. C.; Balbuzano-Deus, A.; Lopez-Lopez, M. A.; Kirsch, G. J. Heterocycl. Chem. 2007, 44, 273.
33. No product formation was observed in the absence of a copper catalyst.
34. Carbon-sulfide bond formation with 2-iodobenzoic acids proved to be complete within two hours, while 2-chlorobenzoic acids gave low yields under the conditions described.
35. (a) Luyt, L. G.; Katzenellenbogen, J. A. Bioconjugate Chem. 2002, 13, 1140.
36. (b) Zarghi, A.; Faizi, M.; Shafaghi, B.; Ahadian, A.; Khojastehpoor, H. R.; Zanganeh, V.; Tabatabai, S. A.; Shafiee, A. Bioorg. Med. Chem. Lett. 2005, 15, 3126.
37. (c) Khan, S.; Bernad, P. L.; Korshun, V. A.; Southern, E. M.; Shchepinov, M. S. Synlett 2005, 2453.
38. (d) Ko, J.; Ham, J.; Yang, I.; Chin, J.; Nam, S.; Kang, H. Tetrahedron Lett. 2006, 47, 7101.
39. Pellon, R. F.; Estevez-Braun, A.; Docampo, M. L.; Martin, A.; Ravelo, A. G. Synlett 2005, 1606.
40. Kirk, K.; Horner, H. A. Biochem. J. 1995, 311, 761.
41. Kohno, Y.; Awano, K.; Miyashita, M.; Fujimori, S.; Kuriyama, K.; Sakoe, Y.; Kudoh, S.; Saito, K.; Kojima, E. Bioorg. Med. Chem. Lett. 1997, 7, 1515.
42. Hiroi, K.; Suzuki, Y.; Abe, I. Tetrahedron: Asymmetry 1999, 10, 1173.
43. Liao, Y.; Venhuis, B. J.; Rodenhuis, N.; Timmerman, W.; Wikstroem, H.; Meier, E.; Bartoszyk, G. D.; Boettcher, H.; Seyfried, C. A.; Sundell, S. J. Med. Chem. 1999, 42, 2235.
44. Parlow, J. J.; Stevens, A. M.; Stegeman, R. A.; Stallings, W. C.; Kurumbail, R. G.; South, M. S. J. Med. Chem. 2003, 46, 4297.
45. Arya, V. P.; Sudarsanam, V. Indian J. Chem., Sect. B: Org. Chem. Inch Med. Chem. 1977, 15, 145.