Fast, efficient and convenient method for the preparation of arylazo sulfides using aryl diazonium silica sulfates under mild and solvent-free conditions

Dyes and Pigments

Volumn 91, Issue 1, 2011, Pages 44-48

  Zarei, Amin ^a   Khazdooz, Leila ^b   Hajipour, Abdol R ^c,d   Aghaei, Hamidreza ^b  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b ISLAMIC AZAD UNIVERSITY   (Iran)

^c UNIVERSITY OF WISCONSIN SCHOOL OF MEDICINE AND PUBLIC HEALTH   (United States)

^d ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Aryl diazonium silica sulfates; Arylazo sulfides; Arylazo thiosulfonates; Mild conditions; Sodium thiolates; Solvent free

Indexed keywords

ARYL DIAZONIUM SILICA SULFATES; ARYLAZO SULFIDES; ARYLAZO THIOSULFONATES; MILD CONDITIONS; SOLVENT-FREE;

FACE RECOGNITION; SODIUM; SOLVENTS; SYNTHESIS (CHEMICAL); TOXIC MATERIALS;

SILICA;

EID: 79952994341     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2011.02.010     Document Type: Article

References (37)

1. A. Roglands, A. Pla-Quintana, and M. Moreno-Mañas Diazonium salts as substrates in palladium-catalyzed cross-coupling reactions Chemical Reviews 106 2006 4622 4643 (Pubitemid 44821997)
2. H. Zollinger Diazo chemistry I 1994 VCH Weinheim
3. H. Zollinger The chemistry of amino, nitroso, nitro and related groups 1996 Wiley and Sons New York
4. G.A. Olah, K.K. Laali, Q. Wang, and G.K.S. Prakash Onium ions 1998 Wiley and Sons New York
5. RN1-like reactions in the gas-phase. A negative-ion mass spectrometric investigation of arylazo sulfides The Journal of Organic Chemistry 61 1996 929 934 (Pubitemid 126585687)
6. RN1 aromatic nucleophilic substitutions The Journal of Organic Chemistry 58 1993 2670 2677
7. T. Suehiro, S. Masuda, T. Tashiro, R. Nakausa, M. Taguchi, and A. Koike Formation and identification of aryldiazenyl radicals using the ESR technique Bulletin of the Chemical Society of Japan 59 1986 1877 1886
8. L.K.H. Van Beek, J.R.G.C.M. Van Beek, J. Boven, and C.J. Schoot Syntheses and cis-trans isomerization of light-sensitive benzenediazo sulfides The Journal of Organic Chemistry 36 1971 2194 2196
9. RN1 approach to diaryl sulfides from arenediazonium tetrafluoroborates Tetrahedron 42 1986 4007 4016
10. RN1 synthesis of aromatic nitriles from diazonium salts via diazo sulfides Tetrahedron 43 1987 4625 4634
11. RN1C-arylation of potassium aryloxides by arylazo phenyl or tert-butyl sulfides in DMSO Tetrahedron 46 1990 7977 7990 (Pubitemid 20383660)
12. RN1 on diazosulfides Tetrahedron 47 1991 333 342
13. RN1 α-arylation and azocoupling reactions Tetrahedron 48 1992 325 334
14. C. Dell'Erba, M. Novi, G. Petrillo, and C. Tavani α-Arylation vs. α-arylhydrazonylation of alkyl aryl ketones with arylazo tert-butyl sulfides Tetrahedron 49 1993 235 242
15. C. Dell'Erba, M. Novi, G. Petrillo, and C. Tavani A novel approach to 1 H-indazoles via arylazosulfides Tetrahedron 50 1994 3529 3536 (Pubitemid 24101605)
16. S.A. Haroutounian, J.P. Dizio, and J.A. Katzenellenbogen Aromatic fluorination by silver-ion promoted decomposition of aryl diazo sulfides: efficient utilization of substoichiometric levels of fluoride ion The Journal of Organic Chemistry 56 1991 4993 4996
17. G. Petrillo, M. Novi, and C. Dell'Erba Unsymmetrical biaryls from aryloxide anions and arylazo phenyl sulfides in DMSO Tetrahedron Letters 30 1989 6911 6912 (Pubitemid 20019652)
18. RN1 approach to some aromatic nitriles via diazosulfides Tetrahedron Letters 28 1987 1345 1348
19. N. Caposcialli, C. Dell'Erba, M. Novi, G. Petrillo, and C. Tavani A novel approach to 1-aryl-2-(p-tolylazo)alkenes from alkyl aryl ketones Tetrahedron 54 1998 5315 5324 (Pubitemid 28204490)
20. L. Bianchi, C. Dell'Erba, M. Maccagno, A. Mugnoli, M. Novi, and G. Petrillo α-Oxohydrazones as imine component in the synthesis of 4-functionalized azetidinones by the Staudinger reaction Tetrahedron 59 2003 10195 10201 (Pubitemid 37490859)
21. A.B. Sakla, N.K. Masoud, Z. Sawiris, and W.S. Ebaid Preparation of diazo phenyl sulfides. Kinetics and mechanism of the diazo coupling reaction of p-nitrobenzenediazo phenyl sulfide with β-naphthol under various conditions Helvetica Chimica Acta 57 1974 481 487
22. T. Yamada, N. Tanaka, T. Morisawa, M. Nishikuri, and A. Kaji Studies of diazosulfides. I. A kinetic study of the reaction of diaryldiazosulfides with β-naphthol in alkaline ethanol Bulletin of the Chemical Society of Japan 43 1970 908 914
23. C.C. Price, and S. Tsunawaki Polycondensation of mercaptobenzenediazonium salts The Journal of Organic Chemistry 85 1963 1867 1868
24. C. Corrado, G. Leandri, and P. Giancarla Synthesis of azothiocompounds and of the intermediate N, N′-thiobisarylamines Ricerca Scientifica 38 1968 35 37
25. A. Zarei, A.R. Hajipour, L. Khazdooz, B.F. Mirjalili, and A. Najafichermahini Rapid and efficient diazotization and diazo coupling reactions on silica sulfuric acid under solvent-free conditions Dyes and Pigments 81 2009 240 244
26. A. Zarei, A.R. Hajipour, and L. Khazdooz A one-pot method for the iodination of aryl amines via stable aryl diazonium silica sulfates under solvent-free conditions Synthesis 2009 941 944
27. A. Zarei, A.R. Hajipour, L. Khazdooz, and H. Aghaei A fast and efficient method for the preparation of aryl azides using stable aryl diazonium silica sulfates under mild conditions Tetrahedron Letters 50 2009 4443 4445
28. A. Zarei, A.R. Hajipour, L. Khazdooz, and H. Aghaei Fast, efficient, and convenient method for the preparation of arylazo aryl sulfones using stable aryldiazonium silica sulfates under mild conditions Synlett 2010 1201 1204
29. 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 2007 81 84 (Pubitemid 46471264)
30. V.D. Filimonov, M. Trusova, P. Postnikov, E.A. Krasnokutskaya, Y.M. Lee, and H.Y. Hwang Unusually stable, versatile, and pure arenediazonium tosylates: their preparation, structures, and synthetic applicability Organic Letters 10 2008 3961 3964
31. D.A. Gorlushko, V.D. Filimonov, E.A. Krasnokutskaya, N.I. Semenischeva, B.S. Go, and H.Y. Hwang Iodination of aryl amines in a water-paste form via stable aryl diazonium tosylates Tetrahedron Letters 49 2008 1080 1082
32. M. Barbero, I. Degani, N. Diulgheroff, S. Dughera, R. Fochi, and M. Migliaccio Alkyl-and arylthiodediazoniations of dry arenediazonium o-benzenedisulfonimides. Efficient and safe modifications of the Stadler and Ziegler reactions to prepare alkyl aryl and diaryl sulfides The Journal of Organic Chemistry 65 2000 5600 5608
33. Y.M. Lee, M.U. Moon, V. Vajpayee, V.D. Filimonov, and K.W. Chi Efficient and economic halogenation of aryl amines via arenediazonium tosylate salts Tetrahedron 66 2010 7418 7422
34. RN1 mechanism ACS monograph 178 1983 American Chemical Society Washington, D.C.
35. J.H. Clark Catalysis of organic reactions by supported inorganic reagents 1994 VCH Weinheim
36. A. Akelah, and A. Moet Functionalized polymers and their applications 1990 Chapman and Hall London
37. P. Hodge, and D.C. Sherrington Polymer-supported reactions in organic synthesis 1980 John Wiley & Sons Chichester