Ninhydrin: an efficient ligand for the Cu-catalyzed N-arylation of nitrogen-containing heterocycles with aryl halides

Tetrahedron Letters

Volumn 49, Issue 6, 2008, Pages 948-951

  Huang, Yi Zheng ^a   Gao, Jin ^a   Ma, Hong ^a   Miao, Hong ^a   Xu, Jie ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Cu catalyzed; N Arylation; Ninhydrin; Nitrogen containing heterocycles

Indexed keywords

BROMIDE; CHLORIDE; COPPER; HALIDE; IMIDAZOLE; IODIDE; IODOBENZENE; LIGAND; NINHYDRIN; NITROGEN;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL STRUCTURE;

EID: 38049027866     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.026     Document Type: Article

References (58)

1. For selected examples, see:. Craig P.N. In: Drayton C.J. (Ed). Comprehensive Medicinal Chemistry Vol. 8 (1991), Pergamon Press, New York
2. Wiglenda T., and Gust R. J. Med. Chem. 50 (2007) 1475
3. Leopoldo M., Lacivita E., Giorgio P.D., Colabufo N.A., Niso M., Berardi F., and Perrone R. J. Med. Chem. 49 (2006) 358
4. Barchechath S.D., Tawatao R.I., Corr M., Carson D.A., and Cottam H.B. J. Med. Chem. 48 (2005) 6409
5. Yoshikawa S., Shinzawa-Itoh K., Nakashima R., Yaono R., Yamashita E., Inoue N., Yao M., Fei M.J., Libeu C.P., Mizushima T., Yamaguchi H., Tomizaki T., and Tsukihara T. Science 280 (1998) 1723
6. For reviews, see:. Nair V., Bindu S., and Sreekumar V. Angew. Chem., Int. Ed. 43 (2004) 5130
7. Hermann W.A. Angew. Chem., Int. Ed. 41 (2002) 1290
8. Ullmann F. Ber. Dtsch. Chem. Ges. 36 (1903) 2382
9. Lindley J. Tetrahedron 40 (1984) 1433
10. For reviews, see:. Corbet J.P., and Mignani G. Chem. Rev. 106 (2006) 2651
11. Beletskaya I.P., and Cheprakov A.V. Coord. Chem. Rev. 248 (2004) 2337
12. Ley S.V., and Thomas A.W. Angew. Chem., Int. Ed. 42 (2003) 5400
13. Kunz K., Scholz U., and Ganzer D. Synlett (2003) 2428
14. Kiyomori A., Marcoux J.F., and Buchwald S.L. Tetrahedron Lett. 40 (1999) 2657
15. Klapars A., Antilla J.C., Huang X.H., and Buchwald S.L. J. Am. Chem. Soc. 123 (2001) 7727
16. Antilla J.C., Klapars A., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 11684
17. Kwong F.Y., and Buchwald S.L. Org. Lett. 5 (2003) 793
18. Antilla J.C., Baskin J.M., Barder T.E., and Buchwald S.L. J. Org. Chem. 69 (2004) 5578
19. Altman R.A., and Buchwald S.L. Org. Lett. 8 (2006) 2779
20. Altman R.A., Koval E.D., and Buchwald S.L. J. Org. Chem. 72 (2007) 6190
21. Verma A.K., Singh J., Sankar V.K., Chaudhary R., and Chandra R. Tetrahedron Lett. 48 (2007) 4207
22. Zhu L.B., Cheng L., Zhang Y.X., Xie R.G., and You J.S. J. Org. Chem. 72 (2007) 2737
23. Sreedhar B., Kumar K.B.S., Srinivas P., Balasubrahmanyam V., and Venkanna G.T. J. Mol. Catal. A: Chem. 265 (2007) 183
24. Xie Y.X., Pi S.F., Wang J., Yin D.L., and Li J.H. J. Org. Chem. 71 (2006) 8324
25. Rao H.H., Jin Y., Fu H., Jiang Y.Y., and Zhao Y.F. Chem. Eur. J. 12 (2006) 3636
26. Liu L.B., Frohn M., Xi N., Dominguez C., Hungate R., and Reider P.J. J. Org. Chem. 70 (2005) 10135
27. Ma H.C., and Jiang X.Z. J. Org. Chem. 72 (2007) 8943
28. Guo X., Rao H.H., Fu H., Jiang Y.Y., and Zhao Y.F. Adv. Synth. Catal. 348 (2006) 2197
29. Lv X., and Bao W.L. J. Org. Chem. 72 (2007) 3863
30. Yang M.H., and Liu F. J. Org. Chem. 72 (2007) 8969
31. Hosseinzadeh R., Tajbakhsh M., and Alikarami M. Tetrahedron Lett. 47 (2006) 5203
32. Lv X., Wang Z.M., and Bao W.L. Tetrahedron 62 (2006) 4756
33. de Lange B., Lambers-Verstappen M.H., van de Vondervoort L.S., Sereinig N., de Rijik R., de Vires A.H.M., and de Vires J.G. Synlett (2006) 3105
34. Hosseinzadeh R., Tajbakhsh M., and Alikarami M. Synlett (2006) 2124
35. Kuil M., Bekedam E.K., Visser G.M., van den Hoogenband A., Terpstra J.W., Kamer P.C.J., van Leeuwen P.W.N.M., and van Strijdonck G.P.F. Tetrahedron Lett. 46 (2005) 2405
36. Zhang H., Cai Q., and Ma D.W. J. Org. Chem. 70 (2005) 5164
37. Cristau H.J., Cellier P.P., Spindler J.F., and Taillefer M. Chem. Eur. J. 10 (2004) 5607
38. Ma D.W., and Cai Q. Synlett (2004) 128
39. Cristau H.J., Cellier P.P., Spindler J.F., and Taillefer M. Eur. J. Org. Chem. (2004) 695
40. Zhang Z.J., Mao J.C., Zhu D., Wu F., Chen H.L., and Wan B.S. Tetrahedron 62 (2006) 4435
41. Zhu D., Wang R.L., Mao J.C., Xu L., Wu F., and Wan B.S. J. Mol. Catal. A: Chem. 256 (2006) 256
42. Xu L., Zhu D., Wu F., Wang R.L., and Wan B.S. Tetrahedron 61 (2005) 6553
43. Zhang Z.J., Mao J.C., Zhu D., Wu F., Chen H.L., and Wan B.S. Catal. Commun. 6 (2005) 784
44. Sperotto E., de Vries J.G., van Klink G.P.M., and van Koten G. Tetrahedron Lett. 48 (2007) 7366
45. Nandurkar N.S., Bhanushali M.J., Bhor M.D., and Bhanage B.M. Tetrahedron Lett. 48 (2007) 6573
46. Chang J.W.W., Xu X.H., and Chan P.W.H. Tetrahedron Lett. 48 (2007) 245
47. Rout L., Jammi S., and Punniyamurthy T. Org. Lett. 9 (2007) 3397
48. Taillefer M., Xia N., and Ouali A. Angew. Chem., Int. Ed. 46 (2007) 934
49. Likhar P.R., Roy S., Roy M., Kantam M.L., and De R.L. J. Mol. Catal. A: Chem. 271 (2007) 57
50. Zhu L.B., Guo P., Li G.C., Lan J.B., Xie R.G., and You J.S. J. Org. Chem. 72 (2007) 8535
51. Kantam M.L., Yadav J., Laha S., Sreedhar B., and Jha S. Adv. Synth. Catal. 349 (2007) 1938
52. Kantam M.L., Rao B.P.C., Choudary B.M., and Reddy R.S. Synlett (2006) 2195
53. Reddy K.R., Kumar N.S., Sreedhar B., and Kantam M.L. J. Mol. Catal. A: Chem. 252 (2006) 136
54. Choudary B.M., Sridhar C., Kantam M.L., Venkanna G.T., and Sreedhar B. J. Am. Chem. Soc. 127 (2005) 9948
55. Son S.U., Park I.K., Park J., and Hyeon T. Chem. Commun. (2004) 778
56. Kantam M.L., Venkanna G.T., Sridhar C., and Kumar K.B.S. Tetrahedron Lett. 47 (2006) 3897
57. Jerphagnon T., van Klink G.P.M., de Vries J.G., and van Koten G. Org. Lett. 7 (2005) 5241
58. 13C NMR, GC/MS (EI), and the melting points of the solid products have also been determined.