Clean and fast oxidative transformation of thiols to disulfides under solvent-free conditions

被引:69
作者
Lenardao, Eder J. [1 ]
Lara, Renata G. [1 ]
Silva, Marcio S. [1 ]
Jacob, Raquel G. [1 ]
Perin, Gelson [1 ]
机构
[1] Univ Fed Pelotas, Inst Quim Geociencias, LASOL, UFPel, BR-96010900 Pelotas, RS, Brazil
关键词
microwave irradiation; solid-supported catalysis; solvent-free reaction; disulfides;
D O I
10.1016/j.tetlet.2007.08.094
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We present here a fast, solvent-free synthesis of symmetrical disulfides using solid supported catalyst (Al-2,O-3/KF). The reaction was performed at room temperature, by gentle heating or under MW irradiation. This efficient and improved method is general for liquid thiols, affording the disulfides in good to excellent yields. The catalytic system can be re-used two times without previous treatment and with comparable activity. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7668 / 7670
页数:3
相关论文
共 26 条
[1]   Simple, extremely fast, and high-yielding oxidation of thiols to disulfides [J].
Alam, A ;
Takaguchi, Y ;
Tsuboi, S .
SYNTHETIC COMMUNICATIONS, 2005, 35 (10) :1329-1333
[2]   Oxidation of thiols to disulfides with molecular bromine on hydrated silica gel support [J].
Ali, MH ;
McDermott, M .
TETRAHEDRON LETTERS, 2002, 43 (35) :6271-6273
[3]   KF/Al2O3 mediated organic synthesis [J].
Blass, BE .
TETRAHEDRON, 2002, 58 (46) :9301-9320
[4]   N-phenyltriazolinedione as an efficient, selective, and reusable reagent for the oxidation of thiols to disulfides [J].
Christoforou, Angelos ;
Nicolaou, Georgia ;
Elemes, Yiannis .
TETRAHEDRON LETTERS, 2006, 47 (52) :9211-9213
[5]  
Cremlyn R. J., 1996, INTRO ORGANOSULFUR C
[6]   Novel conversion of thiols into disulfides, via S-nitrosothiol intermediates using trichloronitromethane [J].
Demir, AS ;
Igdir, AC ;
Mahasneh, AS .
TETRAHEDRON, 1999, 55 (42) :12399-12404
[7]   An environmentally friendly oxidation of thiols to disulfides by calcium hypochlorite and montmorillonite K10 in hexane [J].
Hirano, M ;
Yakabe, S ;
Fukami, M ;
Morimoto, T .
SYNTHETIC COMMUNICATIONS, 1997, 27 (16) :2783-2788
[8]   Oxidative coupling of thiols to disulfides using a solid anhydrous potassium phosphate catalyst [J].
Joshi, AV ;
Bhusare, S ;
Baidossi, M ;
Qafisheh, N ;
Sasson, Y .
TETRAHEDRON LETTERS, 2005, 46 (20) :3583-3585
[9]   1,3-dibromo-5,5-dimethylhydantoin [DBDMH] as an efficient and selective agent for the oxidation of thiols to disulfides in solution or under solvent-free conditions [J].
Khazaei, A ;
Zolfigol, MA ;
Rostami, A .
SYNTHESIS-STUTTGART, 2004, (18) :2959-2961
[10]   A very simple method for the preparation of symmetrical disulfides [J].
Leino, R ;
Lönnqvist, JE .
TETRAHEDRON LETTERS, 2004, 45 (46) :8489-8491