Diethylamine-Catalyzed Dimerization of Thiols: An Inexpensive and Green Method for the Synthesis of Homodisulfides Under Aqueous Conditions

REFERENCES

• (a) Jocelyn , D. C. Biochemistry of the Thiol Group ; Academic Press : New York , 1992 ; (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 γ-turn mimetics replacing amino acid residues 3–5. J. Med. Chem. 1997, 40, 903–919; (c) Palmer, B. D.; Newcastle, G. W.; Thompson, A. M.; Boyd, M.; Showalter, H. D. H.; Sercel, A. D.; Fry, D. W.; Kraker A. J.; Dennyyrosine, W. A. Tyrosine kinase inhibitors, 4: Structure–activity relationships among N- and 3-substituted 2,2′-dithiobis(1H-indoles) for in vitro inhibition of receptor and nonreceptor protein tyrosine kinases. J. Med. Chem. 1995, 38, 58–67 .
   Google Scholar
• Groenewegen , P. ; Kallenberg , H. ; Vandergen , A. Aldehyde enolates, 3: Direct sulfenylation and iodination of aldehyde anions . Tetrahedron Lett . 1979 , 20 , 2817 – 2820 .
   Google Scholar
• Greene , T. W. ; Wuts , P. G. M. Protective Groups in Organic Synthesis ; John Wiley & Sons : New York , 2007 .
   Google Scholar
• 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 .
   Web of Science ®Google Scholar
• (a) Cremlyn , R. J. An Introduction to Organosulfur Chemistry ; John Wiley & Sons : New York , 1996 ; (b) Wiu, D. Recent developments in disulfide bond formation. Synthesis. 2008, 2491–2509 .
   Google Scholar
• (a) Korn , T. J. ; Knochel , P. A direct preparation of functionalized aryl and heteroaryl disulfides from functionalized zinc organometallics by using sulfur monochloride (S2Cl2). Synlett . 2005, 1185–1187; (b) Karimi , B. ; Hazarkhani , H. ; Zareyee , D. Trimethylchlorosilane (TMSCl)– and cyanuric chloride (CC)–catalyzed efficient oxidative coupling of thiols with dimethylsulfoxide. Synthesis . 2002, 2513–2516; (c) Leino , R. ; Lönnqvist , J.-E. A very simple method for the preparation of symmetrical disulfides. Tetrahedron Lett . 2004, 45, 8489–8491; (d) Pathak , U. ; Pandey , L. K. ; Mathur , S. Efficient and convenient oxidation of thiols to symmetrical disulfide with silica-PCl5/NaNO2 in water. Synth. Commun. 2009, 39, 2923–2927.
   Google Scholar
• (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 ; (b) Raghavan , S. ; Rajender , A. ; Joseph , S. C. ; Rasheed , M. A. Catalytic oxidation of thiols to disulfides with vanadyl acetylacetonate (VO(acac)2) . Synth. Commun. 2001 , 31 , 1477 – 1480 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• (a) Tajbakhsh , M. ; Hosseinzadeh , R. ; Shakoori , A. 2,6-Dicarboxypyridinium chlorochromate: An efficient and selective reagent for the oxidation of thiols to disulfides and sulfides to sulfoxides . Tetrahedron Lett . 2004 , 45 , 1889 – 1893 ; (b) HassaniJoshaghani , A. ; Ghammamy , S. ; Bagi , S. ; Moghimi , A. ; Javanshir , Z. Oxidative coupling of thiols to disulfides in solution with tripropylammonium halochromates, (C3H7)3NH[CrO3X], (X˭F, Cl) adsorbed on alumina . Phosphorus, Sulfur Silicon Relat. Elem. 2009 , 184 , 164 – 170 .
   Web of Science ®Google Scholar
• Shaabani , A. ; Tavasoli-Rad , F. ; Lee , D. G. Potassium permanganate oxidation of organic compounds . Synth. Commun. 2005 , 35 , 571 – 580 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Do , Q. T. ; Elothmani , D.; LeGuillanton, G. ; Simonet , J. A new electrochemical method of preparation of unsymmetrical disulfides . Tetrahedron Lett. 1997 , 38 , 3383 – 3384 .
   Web of Science ®Google Scholar
• Kesavan , V. ; Bonnet-Delpon , D. ; Bégué , J.-P. Oxidation in fluoro alcohols: Mild and efficient preparation of disulfides from thiols . Synthesis . 2000 , 223 – 225 .
   Web of Science ®Google Scholar
• Varma , R. S. ; Meshram , H. M. ; Dahiya , R. Solid-state oxidation of thiols to disulfides using ammonium persulfate . Synth. Commun. 2000 , 30 , 1249 – 1255 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• (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 ; (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 ; (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 .
   Web of Science ®Google Scholar
• (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 ; (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 ; (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 .
   Web of Science ®Google Scholar
• (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 β-hydroxy sulfides. Synth. Commun. 2008, 38, 282–289; (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 β-aminoalcohols. Ultrason. Sonochem. 2008, 15, 823–827.
   Web of Science ®Google Scholar
• O'Neil , M. J. (ed.). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals, , 13th ed. ; Merck & Co., Inc. : Whitehouse Station , 2001 .
   Google Scholar
• 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 .
   Google Scholar
• Iranpoor , N. ; Firouzabadi , H. ; Pourali , A.-R. Dinitrogen tetroxide supported on polyvinylpyrrolidone (PVP-N2O4): A new nitrosating and coupling agent for thiols and a selective oxidant for sulfides and disulfides . Tetrahedron. 2000 , 58 , 5179 – 5184 .
   Web of Science ®Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Misra , A. K. ; Agnihotri , G. Nitric acid–mediated oxidative transformation of thiols to disulfides . Synth. Commun. 2004 , 34 , 1079 – 1085 .
   Web of Science ®Google Scholar