New Effective and Environmental Friendly Method for the Hydrodediazoniation of Arenediazonium Tosylates Using Fe-Core/Carbon-Shell Nanoparticles

Abstract:

A simple green method for the hydrodediazoniation of arenediazoniumtosylates in water solutions in the presence of Fe-core/carbon-shell nanoparticles as a reagent was developed. In this course, nanoparticles were used as a hydrogen source, but not water.

• Periodical: Advanced Materials Research (Volume 1040)
• Pages: 263-267
• DOI: https://doi.org/10.4028/www.scientific.net/AMR.1040.263
• Online since: September 2014
• Authors: Maria A. Morozova*, Marina E. Trusova, Ksenia V. Kutonova, Victor D. Filimonov
• Keywords: Aromatic Diazonium Salts, Hydrodediazoniation, Nanoparticle

References

[1] H. Zollinger, Diazo Chemistry I: Aromatic and Heteroaromatic Compounds; VCH: Weinheim, (1994).

[2] R. Pazo-Llorente, H. Maskill, C. Bravo-Diaz and E. Gonzalez-Romero, Dediazoniation of 4-nitrobenzenediazonium ions in acidic MeOH/H2O mixtures: role of acidity and MeOH concentration on the formation of transient diazo ethers that initiate homolytic dediazoniation, Eur. J. Org. Chem. 9 (2006).

DOI: 10.1002/ejoc.200500946

[3] R. Pazo-Llorente, C. Bravo-Diaz and E. Gonzalez-Romero, pH effects on ethanolysis of some arenediazonium ions: evidence for homolytic dediazoniation proceeding through formation of transient diazo ethers, Eur. J. Org. Chem. 15 (2004) 3221–3226.

DOI: 10.1002/ejoc.200400170

[4] W F.W. assmundt, W.F. Kiesman, Detection of aryl radicals in hydrodediazoniations, J. Org. Chem. 62 (1997) 8304 – 8308.

DOI: 10.1021/jo962128y

[5] C. Bravo-Díaz , M E. Romero-Nieto, and E. Gonzalez-Romero, Micellar-promoted homolytic dediazoniation of p-nitrobenzenediazonium Tetrafluoroborate, Langmuir 16 (2000) 42-48.

DOI: 10.1021/la9901682

[6] U. Costas-Costas, C. Bravo-Diaz, E. Gonzalez-Romero, Kinetics and mechanism of the reaction between ascorbic acid derivatives and an arenediazonium salt:  cationic micellar effects, Langmuir 21 (2005) 10983–10991.

DOI: 10.1021/la051564p

[7] C. Bravo-Diaz, E. Gonzalez-Romero, Inhibition of the β-cyclodextrin catalyzed dediazoniation of 4-nitrobenzenediazonium tetrafluoroborate. Blocking effect of sodium dodecyl sulfate, Langmuir 21 (2005) 4888–4895.

DOI: 10.1021/la050111h

[8] K. Daasbjerg, K. Sehested, Reduction of substituted benzenediazonium salts by hydrogen atoms in aqueous acidic solution studied by pulse radiolysis, J. Phys. Chem. A 107 (2003) 4462-4469.

DOI: 10.1021/jp0273732

[9] V.D. Filimonov, P.S. Postnikov, E.A. Krasnokutskaya, Y.M. Lee, H.Y. Hwang, H. Kim and Ki-Whan Chi, Unusually stable, versatile, and pure arenediazonium tosylates: their preparation, structures, and synthetic applicability, Org. Lett. 10 (2008).

DOI: 10.1021/ol8013528

[10] A.E. Ermakov, M.A. Uimin, E.S. Lokteva, A.A. Mysik, S.A. Kachevskii, A.O. Turakulova, V.S. Gaviko, and V.V. Lunin, The synthesis, structure, and properties of carbon-containing nanocomposites based on nickel, palladium, and iron, Russ. J. Phys. Chem. 83 (2009).

DOI: 10.1134/s0036024409070243

[11] E.S. Lokteva, S.A. Kachevskii, A. O. Turakulova, E. V. Golubina, V.V. Lunin, A.E. Ermakov, M.A. Uimin, and A.A. Mysik, The hydrodechlorination of chlorobenzene in the vapor phase in the presence of metal–carbon nanocomposites based on nickel, palladium, and iron, Russ. J. Phys. Chem. A 83 (2009).

DOI: 10.1134/s003602440908010x

[12] A.V. Mekhaev, O.N. Chupakhin, M.A. Uimin, Liquid-phase catalytic hydrodechlorination of aromatic chloro derivatives with metal nanopowders, Rus. Chem. Bull. 58 (2009) 1321- -1324.

DOI: 10.1007/s11172-009-0175-3

[13] P.S. Postnikov, M.E. Trusova, T.A. Fedushchak, M.A. Uimin, A.E. Ermakov, V.D. Filimonov, Aryldiazonium tosylates as new efficient agents for covalent grafting of aromatic groups on carbon coatings of metal nanoparticles, Nanotechnologies in Russia 5 (2010).

DOI: 10.1134/s1995078010070037