Copper-catalyzed amination of aryl halides with nitrogen-containing heterocycle using hippuric acid as the new ligand

Tetrahedron

Volumn 64, Issue 7, 2008, Pages 1383-1387

  Mao, Jincheng ^a   Guo, Jun ^a   Song, Hongliang ^a   Ji, Shun Jun ^a  

^a SOOCHOW UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; CHLORIDE; COPPER; HALIDE; HETEROCYCLIC COMPOUND; HIPPURIC ACID; IMIDAZOLE DERIVATIVE; IODINE DERIVATIVE; LIGAND; MORPHOLINE; NITROGEN;

AMINATION; ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL;

EID: 37649014351     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.11.054     Document Type: Article

References (55)

1. Negwer M. Organic-Chemical Drugs and their Synonyms: An International Survey. 7th ed. (1994), Akademie, Berlin
2. Wolfe J.P., Wagaw S., Marcoux J.-F., and Buchwald S.L. Acc. Chem. Res. 31 (1998) 805-818
3. Hartwig J.F. Angew. Chem., Int. Ed. 37 (1998) 2046-2067
4. Schlummer B., and Scholz U. Adv. Synth. Catal. 346 (2004) 1599-1626
5. Tewari A., Hein M., Zapf A., and Beller M. Tetrahedron 61 (2005) 9705-9709
6. Charles M.D., Schultz P., and Buchwald S.L. Org. Lett. 7 (2005) 3965-3968
7. Nicolaou K.C., Bulger P.G., and Sarlah D. Angew. Chem., Int. Ed. 44 (2005) 4442-4489
8. Shen Q., Shekhar S., Stambuli J.P., and Hartwig J.F. Angew. Chem., Int. Ed. 44 (2005) 1371-1375
9. For reviews see:
10. Lindley J. Tetrahedron 40 (1984) 1433-1456
11. Hassan J., Sevignon M., Gozzi C., Schulz E., and Lemaire M. Chem. Rev. 102 (2002) 1359-1470
12. Ley S.V., and Thomas A.W. Angew. Chem., Int. Ed. 42 (2003) 5400-5449
13. Kunz K., Scholz U., and Ganzer D. Synlett (2003) 2428-2439
14. Gujadhur R.K., Bates C.G., and Venkataraman D. Org. Lett. 3 (2001) 4315-4317
15. Liu L., Frohn M., Xi N., Dominguez C., Hungate R., and Reider P.J. J. Org. Chem. 70 (2005) 10135-10138
16. Klapars A., Antilla J.C., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 123 (2001) 7727-7729
17. Klapars A., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 7421-7428
18. Antilla J.C., Klapars A., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 11684-11688
19. Kwong F.Y., Klapars A., and Buchwald S.L. Org. Lett. 4 (2002) 581-584
20. Enguehard C., Allouchi H., Gueiffier A., and Buchwald S.L. J. Org. Chem. 68 (2003) 4367-4370
21. Jerphagnon T., van Klink G.P.M., de Vries J.G., and van Koten G. Org. Lett. 7 (2005) 5241-5244
22. Ma D., Zhang Y., Yao J., Wu S., and Tao F. J. Am. Chem. Soc. 120 (1998) 12459-12467
23. Ma D., Cai Q., and Zhang H. Org. Lett. 5 (2003) 2453-2455
24. Ma D., and Cai Q. Org. Lett. 5 (2003) 3799-3802
25. Patil M.M., Keelkar A.A., Nabi Z., and Chaudhari R.V. Chem. Commun. (2003) 2460-2461
26. Xu L., Zhu D., Wu F., Wang R., and Wan B. Tetrahedron 61 (2005) 6553-6568
27. Rao H., Jin Y., Fu H., Jiang Y., and Zhao Y. Chem.-Eur. J. 12 (2006) 3636-3646
28. Zhang Z., Mao J., Zhu D., Wu F., Chen H., and Wan B. Catal. Commun. 6 (2005) 784-787
29. Gajare A.S., Toyota K., Yoshifuji M., and Yoshifuji F. Chem. Commun. (2004) 1994-1995
30. Rao H., Fu H., Jiang Y., and Zhao Y. J. Org. Chem. 70 (2005) 8107-8109
31. Xie Y.-X., Pi S.-F., Wang J., Yin D.-L., and Li J.-H. J. Org. Chem. 71 (2006) 8324-8327
32. Cristau H.J., Cellier P.P., Spindler J.F., and Taillefer M. Chem.-Eur. J. 10 (2004) 5607-5622
33. Kelkar A.A., Patil N.M., and Chaudhari R.V. Tetrahedron Lett. 43 (2002) 7143-7146
34. Shafir S., and Buchwald S.L. J. Am. Chem. Soc. 128 (2006) 8742-8743
35. Lv X., and Bao W. J. Org. Chem. 72 (2007) 3863-3867
36. Zhu L., Cheng L., Zhang Y., Xie R., and You J. J. Org. Chem. 72 (2007) 2737-2743
37. Zhu D., Wang R., Mao J., Xu L., Wu F., and Wan B. J. Mol. Catal. A: Chem. 256 (2006) 256-260
38. Jiang D., Fu H., Jiang Y., and Zhao Y. J. Org. Chem. 72 (2007) 672-674
39. Zhang Z., Mao J., Zhu D., Wu F., Chen H., and Wan B. Tetrahedron 62 (2006) 4435-4443
40. Cristau H.J., Cellier P.P., Spindler J.F., and Taillefer M. Chem.-Eur. J. 10 (2004) 5607-5622
41. Zhang H., Cai Q., and Ma D. J. Org. Chem. 70 (2005) 5164-5173
42. Lv X., Wang Z., and Bao W. Tetrahedron 62 (2006) 4756-4761
43. Rao H., Jin Y., Fu H., Jiang Y., and Zhao Y. Chem.-Eur. J. 12 (2006) 3636-3646
44. Kantam M.L., Venkanna G.T., Scridhar C., Sreedhar B., and Choudary B.M. J. Org. Chem. 71 (2006) 9522-9524
45. Liu L., Frohn M., Xi N., Dominguez C., Hungate R., and Reider P.J. J. Org. Chem. 70 (2005) 10135-10138
46. Altman R.A., and Buchwald S.L. Org. Lett. 8 (2006) 2779-2782
47. Rout L., Jammi S., and Punniyamurthy T. Org. Lett. 9 (2007) 3397-3399
48. Taillefer M., Xia N., and Quali A. Angew. Chem., Int. Ed. 46 (2007) 934-936
49. Liu L., Forhn M., Xi N., Dominguez C., Hungate R., and Reider P.J. J. Org. Chem. 70 (2005) 10135-10138
50. For a recent account, see:. Herrmann W.A. Angew. Chem., Int. Ed. 41 (2002) 1290-1309
51. Verma A.K., Singh J., Sankar V.K., Chaudhary R., and Chandra R. Tetrahedron Lett. 48 (2007) 4207-4210
52. Antilla J.C., Baskin J.M., Barder T.E., and Buchwald S.L. J. Org. Chem. 69 (2004) 5578-5587
53. Ma D., and Cai Q. Synlett (2004) 128-130
54. Alcalde E., Dinarès I., Rodrìguez S., and de Miguel C.G. Eur. J. Org. Chem. (2005) 1637-1643
55. Togo H., and Iido S. Synlett (2006) 2159-2175