Green and efficient diazotization-iodination of aryl amines using cellulose sulfuric acid as a biodegradable and recyclable proton source under solvent-free condition

Scientia Iranica

Volumn 19, Issue 6, 2012, Pages 1594-1596

  Nemati, F ^a   Elhampour, A ^a  

^a SEMNAN UNIVERSITY   (Iran)

Author keywords

Aryl amines; Aryl iodides; Biodegradable; Cellulose sulfuric acid; Diazotization

Indexed keywords

CELLULOSE; HALOGENATION; POTASSIUM IODIDE; SODIUM COMPOUNDS; SOLVENTS; SULFURIC ACID;

ARYL AMINES; ARYL IODIDES; BIODEGRADABLE; DIAZOTIZATION; ELECTRON WITHDRAWING GROUP; ELECTRON-DONATING GROUP; MILD REACTION CONDITIONS; SOLVENT FREE CONDITIONS;

AMINES;

BIODEGRADATION; ELECTRON; ENZYME ACTIVITY; SOLVENT; SULFURIC ACID;

EID: 84871944156     PISSN: 10263098     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.scient.2012.10.015     Document Type: Article

References (30)

1. S. Kotha, K. Lahiri, and D. Kashinath Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis Tetrahedron 58 2002 9633 9695
2. W.A. Volkert, and T.J. Hoffman Therapeutic radiopharmaceuticals Chem. Rev. 99 1999 2269 2292
3. S.-B. Yu, and A.D. Watson Metal-based X-ray contrast media Chem. Rev. 99 1999 2353 2378
4. P.E. Fanta The Ullmann synthesis of biaryls Synthesis 1 1974 9 21
5. M.O.S. Otroshchenko, and A.S. Sadykov The Ullmann reaction Russ. Chem. Rev. 41 1972 1046 1059
6. G. Bringmann, R. Walker, and R. Weirich The directed synthesis of biaryl compounds: modern concepts and strategies Angew. Chem. Int. Ed. Engl. 29 1990 977 991
7. N. Miyaura, and A. Suzuki Palladium-catalyzed cross-coupling reactions of organoboron compounds Chem. Rev. 95 1995 2457 2483
8. J.J. Bozell, and C.E. Vogt Bimetallic catalysis, a new method for the activation of chloroarenes toward palladium-catalyzed coupling with olefins J. Am. Chem. Soc. 110 1988 2655 2657
9. R.C. Larock, and P.L. Johnson Palladium-catalysed intermolecular arylation and alkenylation of bicylic alkenes J. Chem. Soc. Chem. Commun. 1989 1368 1369
10. R.C. Larock, W.H. Gong, and B.E. Baker Improved procedures for the palladium-catalyzed intermolecular arylation of cyclic alkenes Tetrahedron Lett. 30 1989 2603 2606
11. S. Patai The Chemistry of Diazonium and Diazo Groups 1978 Wiley New York
12. C. Galli Radical reactions of arenediazonium ions: an easy entry into the chemistry of the aryl radical Chem. Rev. 88 1988 765 792
13. M.P. Doyle, B. Siegfried, and J.F. Dellaria Jr. Alkyl nitrite-metal halide deamination reactions, 2, substitutive deamination of arylamines by alkyl nitrites and copper (II) halides, a direct and remarkably efficient conversion of arylamines to aryl halides J. Org. Chem. 42 1977 2426 2431
14. W. Baik, W. Luan, H.J. Lee, C.H. Yoon, S. Koo, and B.H. Kim Efficient one-pot transformation of aminoarenes to haloarenes using halodimethylisulfonium halides generated in situ Can. J. Chem. 83 2005 213 219
15. E.A. Krasnokutskaya, N.I. Semenischeva, V.D. Filimonov, and P. Knochel A new, one-step, effective protocol for the iodination of aromatic and heterocyclic compounds via aprotic diazotization of amines Synthesis 1 2007 81 84
16. V.D. Filimonov, N.I. Semenischeva, E.A. Krasnokutskaya, A.N. Tretyakov, H.Y. Hwang, and K.-W. Chi Sulfonic acid based cation-exchange resin: a novel proton source for one-pot diazotization-Iodination of aromatic amines in water Synthesis 2 2008 185 187
17. D.A. Gorlushko, V.D. Filimonov, E.A. Krasnokutskaya, N.I. Semenischeva, B.S. Go, H.Y. Hwang, E.H. Cha, and K.-Wh. Chi Iodination of aryl amines in a water-paste form via stable aryl diazonium tosylates Tetrahedron Lett. 49 2008 1080 1082
18. M.E. Trusova, E.A. Krasnokutskaya, P.S. Postnikov, Y. Choi, K.-W. Chi, and V.D. Filimonov A green procedure for the diazotization-iodination of aromatic amines under aqueous, strong-acid-free conditions Synthesis 13 2011 2154 2158
19. A.N. Tretyakov, E.A. Kranokutskaya, D.A. Gorlushko, V.D. Ogorodnikov, and V.D. Filimonov A new one-pot solvent-free synthesis of pyridinyl tosylates via diazotization of aminopyridines Tetrahedron Lett. 52 2011 85 87
20. A. Zarei, A.R. Hajipour, and L. Khazdoozd A one-pot method for the iodination of aryl amines via stable aryl diazonium silica sulfates under solvent-free conditions Synthesis 6 2009 941 944
21. H. Zollinger In Diazo Chemistry I, Aromatic and Heteroaromatic Compounds 1994 VCH 25
22. J.V. Madhav, Y.Th. Reddy, P.N. Reddy, M.N. Reddy, S. Kuarm, P.A. Crooks, and B. Rajitha Cellulose sulfuric acid: an efficient biodegradable and recyclable solid acid catalyst for the one-pot synthesis of aryl-14H-dibenzo[a ṡ j]xanthenes under solvent-free conditions J. Mol. Catal. A: Chem. 304 2009 85 87
23. A. Shaabani, A. Rahmati, and Z. Badri Sulfonated Cellulose and starch: new biodegradable and renewable solid acid catalysts for efficient synthesis of quinolines Catal. Commun. 9 2008 13 16
24. 2O/2, 4, 6-trichloro-1, 3, 5-triazine (TCT) a mild and selective system for nitration of phenols Chin. Chem. Lett. 21 2010 403 406
25. 2O/2, 4, 6-trichloro-1, 3, 5-triazine (TCT) as a mild, selective, and biodegradable system for nitration of phenols Synth. Commun. 41 2011 2985 2992
26. F. Nemati, A.S. Fakhaei, A. Amoozadehm, and Y.S. Hayeniza Highly stereoselective synthesis of β-amino ketones via a Mannich reaction catalyzed by Cellulose sulfuric acid as a biodegradable, efficient and recyclable heterogeneous catalyst Synth. Commun. 41 2011 3695 3702
27. Aldrich handbook of fine chemicals
28. Organic Syntheses, Coll., 2, p. 353 (1943).
29. 4 at room temperature Iran. J. Chem. Eng. 30 2011 23 28
30. M.A. Karimi Zarchi, and N. Ebrahimi Diazotization-iodination of aromatic amines in water mediated by crosslinked poly(4-vinylpyridine) supported sodium nitrite J. App. Polym. Sci. 121 2011 2621 2625