Chemo- and regioselective reduction of nitroarenes, carbonyls and azo dyes over nickel-incorporated hexagonal mesoporous aluminophosphate molecular sieves

Tetrahedron Letters

Volumn 45, Issue 9, 2004, Pages 2003-2007

  Selvam, Parasuraman ^a   Mohapatra, Susanta K ^a   Sonavane, Sachin U ^b   Jayaram, Radha V ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

^b UNIVERSITY OF MUMBAI   (India)

Author keywords

Carbonyl compounds; Catalytic transfer hydrogenation; Mesoporous molecular sieves; Nickel; Nitro compounds

Indexed keywords

ALUMINUM PHOSPHATE; AROMATIC NITRO COMPOUND; AZO DYE; CARBONYL DERIVATIVE; HYDROGEN; NICKEL COMPLEX;

ARTICLE; CATALYST; ION TRANSPORT; METHODOLOGY; POROSITY; REDUCTION;

EID: 1242338904     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.12.091     Document Type: Article

References (36)

1. Kabalka G.W., Verma R.S. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 8:1991;363 Pergamon, Oxford.
2. Merlic C.A., Motamed S., Quinn B. J. Org. Chem. 60:1995;3365.
3. Johnstone R.A.W., Wilby A.H., Entwistle I.D. Chem. Rev. 85:1985;129.
4. Zassinovich G., Mestroni G., Gladiali S. Chem. Rev. 92:1992;1051.
5. For a monograph, see: Hudlicky M. Reduction in Organic Chemistry. 2nd ed. 1996;ACS, Washington, DC.
6. Andrews M.J., Pillai C.N. Indian J. Chem. B. 16:1978;465.
7. Ayyanger N.R., Lugade A.G., Nikrad P.V., Sharma V.K. Synthesis. 1981;640.
8. Gilchrist T.L. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 8:1991;388 Pergamon, Oxford.
9. Upadhya T.T., Ramaswamy V., Sabade D.P., Katdure D.P., Sudalai A. Chem. Commun. 1997;1119.
10. Sonavane S.U., Jayaram R.V. Synth. Commun. 33:2003;843.
11. Kimura T., Sugahara Y., Kuroda K. Chem. Mater. 11:1999;508.
12. Kresge C.T., Leonowicz M.E., Roth W.T., Vartuli J.C., Beck J.S. Nature. 359:1992;710.
13. Selvam P., Bhatia S.K., Sonwane C.G. Ind. Eng. Chem. Res. 40:2001;3237.
14. Mohapatra S.K., Sahoo B., Keune W., Selvam P. Chem. Commun. 2002;1466.
15. Mohapatra S.K., Selvam P. Top. Catal. 22:2003;17.
16. Mohapatra S.K., Hussain F., Selvam P. Catal. Commun. 4:2003;57.
17. 3-TPD) confirmed the presence of Lewis acid sites in the catalyst (desorption band around 873 K).
18. 2, followed by 2 h in air.
19. -1; and pore size, 26 Å) support the mesoporous nature of the sample. ICP-AES analysis shows 3.5 wt% Ni loading in the catalyst.
20. In a typical CTH reaction, KOH pellets (20 mmol) were dissolved in propan-2-ol (20 mL) to which the substrate (20 mmol) was added along with 100 mg of catalyst. It was then refluxed at 356 K for a few hours depending upon the nature of the substrate. The products were analyzed using a gas chromatograph (Eshika) fitted with an OV-101 column. For recycling purposes, the catalyst after filtration was washed several times with acetone followed by thorough washing with water to remove any alkali; it was then activated at 373 K and reused.
21. Mohapatra S.K., Sonavane S.U., Jayaram R.V., Selvam P. Tetrahedron Lett. 43:2002;8527. 2003, 44, 1107.
22. Mohapatra S.K., Sonavane S.U., Jayaram R.V., Selvam P. Org. Lett. 4:2002;4297. 2003, 5, 233.
23. Iyer S., Varghese J.P. J. Chem. Soc., Chem. Commun. 1995;465.
24. Le Page M.D., James B.R. Chem. Commun. 2000;1647.
25. Gilchrist T.L. Trost B.M., Fleming I. Comprehensive Organic Synthesis. Vol. 8:1991;381 Pergamon, Oxford.
26. Gowda S., Abiraj K., Gowda D.C. Tetrahedron Lett. 43:2002;1329.
27. 2 (7.85% Ni) under identical reaction conditions, which gave a >95% yield in the first run, and 83% yield for the sixth run.
28. The effect of various hydrogen donors such as primary and secondary alcohols on the CTH of nitrobenzene was performed over NiHMA. The former gave lower yields (methanol/11%; ethanol/23%; propan-1-ol/72%; butan-1-ol/55%; pentan-1-ol/46%; octan-1-ol/30%) while the latter (propan-2-ol/97%; butan-2-ol/87%) gave higher yields of aniline. In addition, the dehydrogenation product is a ketone, which can easily be removed from the reaction system. In the case of tertiary alcohols, for example, 2-methylpropan-1-ol, the reaction did not proceed as there is no α-hydrogen and hence they cannot act as hydrogen donors. Therefore, in this study, we used propan-2-ol as the hydrogen donor.
29. de Graauw C.F., Peters J.A., van Bekkum H., Huskens J. Synthesis. 1994;1007.
30. Quignard F., Graziani O., Choplin A. Appl. Catal. A. 182:1999;29.
31. Ho T.L., Olah G.A. Synthesis. 1977;169.
32. Creyghton E.J., Ganeshie S.D., Downing R.S., van Bekkum H. J. Mol. Catal. A. 115:1997;457.
33. van der Waal J.C., Kunkeler P.J., Tan K., van Bekkum H. J. Catal. 173:1998;74.
34. Creyghton E.J., Downing R.S. J. Mol. Catal. A. 134:1998;47.
35. Zassinovich G., Mestroni G. Chem. Rev. 92:1992;1051.
36. Aramendia M.A., Borau V., Gomez J., Jimenez C., Maranas J.M. Appl. Catal. 10:1984;347.