A convenient and selective catalytic method for the sulfoxidation of aliphatic and aromatic sulfides by treatment of NH4NO3, silica sulfuric acid, wet SiO2 (50% w/w) and a catalytic amount of KBr in CH2Cl2 at room temperature was developed. Many sulfides can be selectively oxidized at room temperature in good to excellent yields. The reaction proceeds without over-oxidation to sulfones under mild conditions.
参考文献
| [1] | Hiroi K.;Abe I.;Kawagishi R.;Suzuki Y. .New chiral sulfoxide ligands possessing a phosphano or phosphanoamino functionality in palladium-catalyzed asymmetric allylic nucleophilic substitution reactions[J].Tetrahedron,2000(27):4701-4710. |
| [2] | Carreno M C .[J].Chemical Reviews,1995,95:1717. |
| [3] | Fernandez I;Khiar N .[J].Chemical Reviews,2003,103:3651. |
| [4] | Hajipour AR.;Hantehzadeh M. .Preparation of R-(+)-3,4-dimethoxybenzyl, 2-methoxy-1-naphthyl sulfoxide and diastereoselective addition of lithiated anion of this reagent to cyclic nitrone. Asymmetric synthesis of optical pure isoquinoline alkaloids[J].Phosphorus, Sulfur, and Silicon and the Related Elements,2000(0):181-189. |
| [5] | Shapiro N D;Toste F D .[J].Journal of the American Chemical Society,2007,129:4160. |
| [6] | Hajipour AR. .STEREOCHEMISTRY OF THE ADDITION OF LITHIATED METHYL PHENYL SULFOXIDE TO OXAZIRIDINES[J].Synthetic Communications,1996(19):3627-3632. |
| [7] | Posner G H;Weitzberg M;Hamill T G;Asirvatham E He C H Clardy J .[J].Tetrahedron,1986,42:2919. |
| [8] | Kosugi H;Watanabe Y;Uda H .[J].Chemistry Letters,1989,18:1865. |
| [9] | Hosseinpoor F;Golchoubian H .Mn(III)-catalyzed oxidation of sulfides to sulfoxides with hydrogen peroxide[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,2006(29):5195-5197. |
| [10] | Gao A;Wang M;Shi J;Wang D Tian W Sun L .[J].Applied Organometallic Chemistry,2006,20:830. |
| [11] | Imada Y;Ohno T;Naota T .[J].Tetrahedron Letters,2007,48:937. |
| [12] | Lakouraj M M;Tajbakhsh M;Tashakkorian H .[J].Monatshefte Fur Chemie,2007,138:83. |
| [13] | Gao A P;Wang M;Wang D D;Zhang L Liu H B Tian W Sun L Ch .[J].Chinese Journal of Catalysis,2006,27:743. |
| [14] | Surendra K;Krishnaveni N S;Kumar V P;Sridhar R Rao K R .[J].Tetrahedron Letters,2005,46:4581. |
| [15] | Ali MH;Stricklin S .Oxidation of sulfides with pyridinium tribromide in the presence of hydrated silica gel[J].Synthetic Communications,2006(12):1779-1786. |
| [16] | Meshram H M;Ganesh Y S S;Madhavi A V;Eshwaraiah B Yadav J S Gunasekar D .[J].Synthetic Communications,2003,33:2497. |
| [17] | Meshram H M;Sumithra G;Reddy G S;Ganesh Y S S Yadav J S .[J].Synthetic Communications,1999,29:2807. |
| [18] | Yadav J S;Meshram H M;Reddy G S;Sumithra G .[J].Tetrahedron Letters,1998,39:3043. |
| [19] | Doxsee KM.;Weakley TJR.;Francis PE. .Hydration, ion pairing, and sandwich motifs in ammonium nitrate complexes of crown ethers[J].Tetrahedron,2000(36):6683-6691. |
| [20] | Zolfigol MA;Bagherzadeh M;Mallakpour S;Chehardoli G;Ghorbani-Choghamarani A;Koukabi N;Dehghanian M;Doroudgar M .The first report on the catalytic oxidation of urazoles to their corresponding triazolinediones via in situ catalytic generation of Br+ using periodic acid or Okone (R)/KBr system[J].Journal of molecular catalysis, A. Chemical,2007(1/2):219-224. |
| [21] | Zolfigol MA;Shirini F;Chehardoli G .A catalytic and transition metal-free method for the chemoselective oxidation of alcohols to their corresponding carbonyl compounds using periodic acid or iodic acid in the presence of a catalytic amount of KBr[J].Journal of molecular catalysis, A. Chemical,2007(1/2):272-275. |
| [22] | Zolfigol M A;Amani K;Ghorbani-Choghamarani A;Hajjami M Ayazi-Nasrabadi R Jafari S .[J].Catalysis Communications,2008,9:1739. |
| [23] | Zolfigol M A;Amani K;Hajjami M;Ghorbani-Choghamarani A .[J].Monatshefte fur Chemie,2008,139:895. |
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