Diethylamine-catalyzed dimerization of thiols: An inexpensive and green method for the synthesis of homodisulfides under aqueous conditions

Synthetic Communications

Volumn 41, Issue 2, 2011, Pages 170-176

  Abaee, M Saeed ^a   Mojtahedi, Mohammad M ^a   Navidipoor, Somayeh ^a  

^a CHEMISTRY AND CHEMICAL ENGINEERING RESEARCH CENTER OF IRAN   (Iran)

Author keywords

Aqueous conditions; disulfides; oxidation; thiols

Indexed keywords

ALIPHATIC THIOL; AROMATIC THIOL; BENZYLIC THIOL; DIETHYLAMINE; OXYGEN; THIOL; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; CATALYSIS; DIMERIZATION; SYNTHESIS;

EID: 78650296352     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903531904     Document Type: Article

References (36)

1. (a) Jocelyn, D. C. Biochemistry of the Thiol Group; Academic Press: New York, 1992;
2. (b) Schmidt, B.; Lindman, S.; Tong, W.; Lindeberg, G.; Gogoll, A.; Lai, Z.; Thornwall, M.; Synnergren, B.; Nilson, A.; Welch, C. J.; Sohtell, M.; Westerlund, C.; Nyberg, F.; Karlen A.; Hallberg, A. Design, synthesis, and biological activities of four angiotensin II receptor ligands with c-turn mimetics replacing amino acid residues 3-5. J. Med. Chem. 1997, 40, 903-919;
3. 0 -dithiobis-(1H-indoles) for in vitro inhibition of receptor and nonreceptor protein tyrosine kinases. J. Med. Chem. 1995, 38, 58-67.
4. Groenewegen, P.; Kallenberg, H.; Vandergen, A. Aldehyde enolates, 3: Direct sulfenyla-tion and iodination of aldehyde anions. Tetrahedron Lett. 1979, 20, 2817-2820.
5. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley & Sons: New York, 2007.
6. Tsuboi, T.; Takaguchi, Y.; Tsuboi, S. Novel photoreaction using diphenyl disulfide derivatives: Photoinduced oxidation of allyl alcohol. Bull. Chem. Soc. Jpn. 2008, 81, 361-368.
7. (a) Cremlyn, R. J. An Introduction to Organosulfur Chemistry; John Wiley & Sons: New York, 1996;
8. (b) Wiu, D. Recent developments in disulfide bond formation. Synthesis. 2008, 2491-2509.
9. 2). Synlett. 2005, 1185-1187;
10. (b) Karimi, B.; Hazarkhani, H.; Zareyee, D. Trimethylchlorosi-lane (TMSCl)- and cyanuric chloride (CC)-catalyzed efficient oxidative coupling of thiols with dimethylsulfoxide. Synthesis. 2002, 2513-2516;
11. (c) Leino, R.; Lönnqvist, J.-E. A very simple method for the preparation of symmetrical disulfides. Tetrahedron Lett. 2004, 45, 8489-8491;
12. 2 in water. Synth. Commun. 2009, 39, 2923-2927.
13. (a) Shah, S. T. A.; Khan, K. M.; Feckera, M.; Voelter, W. A novel method for the syntheses of symmetrical disulfides using CsF-celite as a solid base. Tetrahedron Lett. 2003, 44, 6789-6791;
14. 2). Synth. Commun. 2001, 31, 1477-1480.
15. Bourles, E.; Sousa, R. A.; Galardon, E.; Selkti, M.; Tomas, A.; Artaud, I. Synthesis of cyclic mono- and bis-disulfides and their selective conversion to mono- and bis-thiosulfinates. Tetrahedron. 2007, 63, 2466-2471.
16. (a) Tajbakhsh, M.; Hosseinzadeh, R.; Shakoori, A. 2,6-Dicarboxypyridinium chlorochro-mate: An efficient and selective reagent for the oxidation of thiols to disulfides and sulfides to sulfoxides. Tetrahedron Lett. 2004, 45, 1889-1893;
17. 3X], (X=F, Cl) adsorbed on alumina. Phosphorus, Sulfur Silicon Relat. Elem. 2009, 184, 164-170.
18. Shaabani, A.; Tavasoli-Rad, F.; Lee, D. G. Potassium permanganate oxidation of organic compounds. Synth. Commun. 2005, 35, 571-580.
19. Sridhar, M.; Vadivel, S. K.; Bhalerao, U. T. Novel method for preparation of symmetric disulfides from thiols using enzyme catalysis. Synth. Commun. 1998, 28, 1499-1502.
20. Do, Q. T.; Elothmani, D.; LeGuillanton, G.; Simonet, J. A new electrochemical method of preparation of unsymmetrical disulfides. Tetrahedron Lett. 1997, 38, 3383-3384.
21. Kesavan, V.; Bonnet-Delpon, D.; Bégué, J.-P. Oxidation in fluoro alcohols: Mild and efficient preparation of disulfides from thiols. Synthesis. 2000, 223-225.
22. Varma, R. S.; Meshram, H. M.; Dahiya, R. Solid-state oxidation of thiols to disulfides using ammonium persulfate. Synth. Commun. 2000, 30, 1249-1255.
23. Saxena, A.; Kumar, A.; Mozumdar, S. Ni-nanoparticles: An efficient green catalyst for chemoselective oxidative coupling of thiols. J. Mol. Catal. A: Chem. 2007, 269, 35-40.
24. (a) Ruano, J. L. G.; Parra, A.; Alemán, J. Efficient synthesis of disulfides by air oxidation of thiols under sonication. Green Chem. 2008, 10, 706-711;
25. (b) Walters, M. A.; Chaparro, J.; Siddiqui, T.; Williams, F.; Ulku, C.; Rheingold, A. L. The formation of disulfides by the [Fe(nta)Cl-2](2-) catalyzed air oxidation of thiols and dithiols. Inorg. Chim. Acta. 2006, 359, 3996-4000;
26. (c) Dong, W.-L.; Huang, G.-Y.; Li, Z.-M.; Zhao, W.-G. A convenient method for the aerobic oxidation of thiols to disulfides. Phosphorus, Sulfur Relat. Elem. 2009, 184, 2058-2065.
27. (a) Mojtahedi, M. M.; Abaee, M. S.; Heravi, M. M.; Behbahani, F. K. Additive-free chemoselective acylation of amines and thiols. Monatsh. Chem. 2007, 138, 95-99;
28. (b) Mojtahedi, M. M.; Akbarzadeh, E.; Sharifi, R.; Abaee, M. S. Lithium bromide as a flexible, mild, and recyclable reagent for solvent-free Cannizzaro, Tishchenko, and Meerwein-Ponndorf-Verley reactions. Org. Lett. 2007, 9, 2791-2793;
29. (c) Mojtahedi, M. M.; Javadpour, M.; Abaee, M. S. Convenient ultrasound-mediated synthesis of substituted pyrazolones under solvent-free conditions. Ultrason. Sonochem. 2008, 15, 828-832.
30. (a) Abaee, M. S.; Mojtahedi, M. M.; Abbasi, H.; Fatemi, E. R. Additive-free thiolysis of epoxides in water: A green and efficient regioselective pathway to b-hydroxy sulfides. Synth. Commun. 2008, 38, 282-289;
31. (b) Abaee, M. S.; Hamidi, V.; Mojtahedi, M. M. Ultrasound-promoted aminolysis of epoxides in aqueous media: A rapid procedure with no pH adjustment for additive-free synthesis of b-aminoalcohols. Ultrason. Sonochem. 2008, 15, 823-827.
32. O'Neil, M. J. (ed.). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, 13th ed.; Merck & Co., Inc.: Whitehouse Station, 2001.
33. Su, W.; Gao, N.; Zhang, Y.; Zhu, J. Ytterbium metal-promoted reaction of disulfides with 2-oxoimidazolidine-1-carbonyl chlorides. J. Chem. Res. 2002, 442-443.
34. 4): A new nitrosating and coupling agent for thiols and a selective oxidant for sulfides and disulfides. Tetrahedron. 2000, 58, 5179-5184.
35. Lenardão, E. J.; Lara, R. G.; Silva, M. S.; Jacob, R. G.; Perin, G. Clean and fast oxidative transformation of thiols to disulfides under solvent-free conditions. Tetrahedron Lett. 2007, 48, 7668-7670.
36. Misra, A. K.; Agnihotri, G. Nitric acid-mediated oxidative transformation of thiols to disulfides. Synth. Commun. 2004, 34, 1079-1085.