Polyaniline supported CuI: An efficient catalyst for C-N bond formation by N-arylation of N(H)-heterocycles and benzyl amines with aryl halides and arylboronic acids, and aza-Michael reactions of amines with activated alkenes

Catalysis Communications

Volumn 9, Issue 13, 2008, Pages 2226-2230

  Kantam, M Lakshmi ^a   Roy, Moumita ^a   Roy, Sarabindu ^a   Sreedhar, Bojja ^a   Lal De, Rajib ^b  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

^b JADAVPUR UNIVERSITY   (India)

Author keywords

Aza Michael reaction; Copper; N arylation; Polyaniline; Reusable catalyst

Indexed keywords

ACIDS; ADDITION REACTIONS; AMINATION; AMINES; AROMATIC COMPOUNDS; CATALYSIS; CATALYST ACTIVITY; FILTRATION; HYDROCARBONS; OLEFINS; ORGANIC COMPOUNDS; POROUS MATERIALS;

(Z) ALKENES; ARYL BORONIC ACIDS; ARYL HALIDES; AZA MICHAEL REACTIONS; BENZYLAMINES; C-N BOND; ELSEVIER (CO); HETERO-CYCLES; N-ARYLATION;

REACTION KINETICS;

EID: 46449090815     PISSN: 15667367     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.catcom.2008.04.023     Document Type: Article

References (35)

1. Cozzi P., Carganico G., Fusar D., Grossoni M., Menichincheri M., Pinciroli V., Tonani R., Vaghi F., and Salvati P. J. Med. Chem. 36 (1993) 2964
2. Jacobs C., Frotscher M., Dannhardt G., and Hartmann R.W. J. Med. Chem. 43 (2000) 1841
3. Lam P.Y.S., Clark C.G., Saubern S., Adams J., Winters M.P., Chan D.M.T., and Combs A. Tetrahedron Lett. 39 (1998) 2941
4. Collman J.P., Zhong M., Zhang C., and Costanzo S. J. Org. Chem. 66 (2001) 7892
5. Kiyomori A., Marcoux J.F., and Buchwald S.L. Tetrahedron Lett. 40 (1999) 2657
6. Klapars A., Antilla J.C., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 123 (2001) 7727
7. Antilla J.C., Klapars A., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 11684
8. Antilla J.C., Baskin J.M., Barder T.E., and Buchwald S.L. J. Org. Chem. 69 (2004) 5578
9. Cristau H.J., Cellier P.P., Spindler J.F., and Taillefer M. Eur. J. Org. Chem. (2004) 695
10. Cristau H.J., Cellier P.P., Spindler J.F., and Taillefer M. Chem. Eur. J. 10 (2004) 5607
11. Cai Q., Zhu W., Zhang H., Zhang Y., and Ma D. Synthesis (2005) 496
12. Choudary B.M., Sridhar C., Kantam M.L., Venkanna G.T., and Sreedhar B. J. Am. Chem. Soc. 127 (2005) 9948
13. Kantam M.L., Rao B.P.C., Choudary B.M., and Reddy R.S. Synlett (2006) 2195
14. Reddy K.R., Kumar N.S., Sreedhar B., and Kantam M.L. J. Mol. Catal. A: Chem. 252 (2006) 136
15. Likhar P.R., Roy S., Roy M., Kantam M.L., and Lal De R. J. Mol. Catal. A: Chem. 271 (2007) 58
16. Son S.U., Park I.K., Park J., and Hyeon T. Chem. Commun. (2004) 778
17. Rout L., Jammi S., and Punniyamurthy T. Org. Lett. 9 (2007) 3397
18. Huang Y.-Z., Miao H., Zhang Q.-H., Chen C., and Xu J. Catal. Lett. 122 (2008) 344
19. Yi J., Zou J., Lei H., Liu X., and Zhang M. Org. Prep. Proced. Int. 23 (1991) 673
20. Graul A., and Castaner J. Drugs Future 22 (1997) 956
21. Bull S.D., Davies S.G.S., Ballester D., Fenton G., Kelly P.M., and Smith A.D. Synlett (2000) 1257
22. Davies S.G., and McCarthy T.D. Synlett (1995) 700
23. Rosenthal D., Brandrup G., Davis K.H., and Wall M.E. J. Org. Chem. 30 (1965) 3689
24. Shaikh N.S., Despande V.H., and Bedekar A.V. Tetrahedron 57 (2001) 9045
25. Yang L., Xu L.-W., and Xia C.G. Tetrahedron Lett. 46 (2005) 3279
26. Zhang H., Zhang Y., Liu L., Xu H., and Wang Y. Synthesis (2005) 2129
27. Reddy K.R., and Kumar N.S. Synlett (2006) 2246
28. Skoheim T.A., Elsenbaumer R.L., and Reynolds J.R. Handbook of Conducting Polymers. second ed. (1998), Marcel Dekker, New York
29. Velusamy S., Ahamed M., and Punniyamurthy T. Org. Lett. 6 (2004) 4821
30. Prabhakaran E.N., and Iqbal J. J. Org. Chem. 64 (1999) 3339
31. Choudary B.M., Roy M., Roy S., Kantam M.L., Sreedhar B., and Kumar K.V. Adv. Synth. Catal. 348 (2006) 1734
32. Ping Z., Nauer G.E., Neugebauer H., Theiner J., and Neckel A. J. Chem. Soc. Faraday Trans. 93 (1997) 121
33. Moulder J.F., Stickle W.F., Sobol P.E., and Bomden K.D. Handbook of X-ray Photoelectron Spectroscopy (1992), Perkin-Elmer Corp.
34. Verma A.K., Kumar R., Chaudhary P., Saxena A., Shankar R., Mazumdar S., and Chandra R. Tetrahedron Lett. 46 (2005) 5229
35. Xu L.W., Li J.W., Xia C.G., Zhou S.L., and Hu X.X. Synlett (2003) 2425