
Fe(NO3)3·9H2O-catalyzed aerobic oxidation of sulfi des to sulfoxides under mild conditions with the aid of trifl uoroethanol
-
关键词:
- Fe(NO3)3·9H2O
- / TFE
- / Oxidation
- / Sulfoxides
English
Fe(NO3)3·9H2O-catalyzed aerobic oxidation of sulfi des to sulfoxides under mild conditions with the aid of trifl uoroethanol
-
Key words:
- Fe(NO3)3·9H2O
- / TFE
- / Oxidation
- / Sulfoxides
-
-
[1] I. Fernández, N. Khiar, Recent developments in the synthesis and utilization of chiral sulfoxides, Chem. Rev. 103 (2003) 3651-3706.[1] I. Fernández, N. Khiar, Recent developments in the synthesis and utilization of chiral sulfoxides, Chem. Rev. 103 (2003) 3651-3706.
-
[2] E. Wojaczynska, J. Wojaczynski, Enantioselective synthesis of sulfoxides: 2000- 2009, Chem. Rev. 110 (2010) 4303-4356.[2] E. Wojaczynska, J. Wojaczynski, Enantioselective synthesis of sulfoxides: 2000- 2009, Chem. Rev. 110 (2010) 4303-4356.
-
[3] (a) J. Legros, J.R. Dehli, C. Bolm, Applications of catalytic asymmetric sulfide oxidations to the syntheses of biologically active sulfoxides, Adv. Synth. Catal. 347 (2005) 19-31;[3] (a) J. Legros, J.R. Dehli, C. Bolm, Applications of catalytic asymmetric sulfide oxidations to the syntheses of biologically active sulfoxides, Adv. Synth. Catal. 347 (2005) 19-31;
-
[4]
(b) J.E. Bäckvall, Modern Oxidation Methods, Wiley-VCH, Weinheim, Germany, 2010;(b) J.E. Bäckvall, Modern Oxidation Methods, Wiley-VCH, Weinheim, Germany, 2010;
-
[5]
(c) M. Bakavoli, A.M. Kakhky, A. Shiri, et al., Selective and mild oxidation of sulfides to sulfoxides by H2O2 using DBUH-Br3 as catalyst, Chin. Chem. Lett. 21 (2010) 651-655;(c) M. Bakavoli, A.M. Kakhky, A. Shiri, et al., Selective and mild oxidation of sulfides to sulfoxides by H2O2 using DBUH-Br3 as catalyst, Chin. Chem. Lett. 21 (2010) 651-655;
-
[6]
(d) A. Ghorbani-Choghamarani, M. Abbasi, Poly(4-vinylpyridinium tribromide) as metal-free, green and recoverable oxidizing polymer for the chemoselective oxidation of sulfides into sulfoxides, Chin. Chem. Lett. 22 (2011) 114-118.(d) A. Ghorbani-Choghamarani, M. Abbasi, Poly(4-vinylpyridinium tribromide) as metal-free, green and recoverable oxidizing polymer for the chemoselective oxidation of sulfides into sulfoxides, Chin. Chem. Lett. 22 (2011) 114-118.
-
[4] S.L. Jain, B.S. Rana, B. Singh, et al., An improved high yielding immobilization of vanadium Schiff base complexes on mesoporous silica via azide-alkyne cycloaddition for the oxidation of sulfides, Green Chem. 12 (2010) 374-377.[4] S.L. Jain, B.S. Rana, B. Singh, et al., An improved high yielding immobilization of vanadium Schiff base complexes on mesoporous silica via azide-alkyne cycloaddition for the oxidation of sulfides, Green Chem. 12 (2010) 374-377.
-
[5] (a) M. Hirano, S. Yakabe, J.H. Clark, K. Hiroyuki, M. Takashi, Manganese(III)- catalysed oxidation of sulphides with sodium chlorite in an aprotic solvent in the presence of alumina, Synth. Commun. 26 (1996) 1875-1886;[5] (a) M. Hirano, S. Yakabe, J.H. Clark, K. Hiroyuki, M. Takashi, Manganese(III)- catalysed oxidation of sulphides with sodium chlorite in an aprotic solvent in the presence of alumina, Synth. Commun. 26 (1996) 1875-1886;
-
[9]
(b) F. Voss, E. Herdtweck, T. Bach, Hydrogen bond induced enantioselectivity in Mn(salen)-catalysed sulfoxidaton reactions, Chem. Commun. 47 (2011) 2137-2139.(b) F. Voss, E. Herdtweck, T. Bach, Hydrogen bond induced enantioselectivity in Mn(salen)-catalysed sulfoxidaton reactions, Chem. Commun. 47 (2011) 2137-2139.
-
[6] B.M. Choudary, C.R.V. Reddy, B.V. Prakash, M.L. Kantam, B. Sreedhar, The first example of direct oxidation of sulfides to sulfones by an osmate molecular oxygen system, Chem. Commun. 39 (2003) 754-755.[6] B.M. Choudary, C.R.V. Reddy, B.V. Prakash, M.L. Kantam, B. Sreedhar, The first example of direct oxidation of sulfides to sulfones by an osmate molecular oxygen system, Chem. Commun. 39 (2003) 754-755.
-
[7] M. Matteucci, G. Bhalay, M. Bradley, Mild and highly chemoselective oxidation of thioethers mediated by Sc(OTf)3, Org. Lett. 5 (2003) 235-237.[7] M. Matteucci, G. Bhalay, M. Bradley, Mild and highly chemoselective oxidation of thioethers mediated by Sc(OTf)3, Org. Lett. 5 (2003) 235-237.
-
[8] M.A.M. Capozzi, C. Centrone, G. Fracchiolla, F. Nsao, C. Cardelliccio, A study of factors affecting enantioselectivity in the oxidation of aryl benzyl sulfides in the presence of chiral titanium catalysts, Eur. J. Org. Chem. 23 (2011) 4327-4334.[8] M.A.M. Capozzi, C. Centrone, G. Fracchiolla, F. Nsao, C. Cardelliccio, A study of factors affecting enantioselectivity in the oxidation of aryl benzyl sulfides in the presence of chiral titanium catalysts, Eur. J. Org. Chem. 23 (2011) 4327-4334.
-
[9] J.B. Arterburn, S.L. Nelson, Rhenium-catalyzed oxidation of sulfides with phenyl sulfoxide, J. Org. Chem. 61 (1996) 2260-2261.[9] J.B. Arterburn, S.L. Nelson, Rhenium-catalyzed oxidation of sulfides with phenyl sulfoxide, J. Org. Chem. 61 (1996) 2260-2261.
-
[10] P.J. Chai, Y.S. Li, C.X. Tan, An efficient and convenient method for preparation of disulfides from thiols using air as oxidant catalyzed by Co-salophen, Chin. Chem. Lett. 22 (2011) 1403-1406.[10] P.J. Chai, Y.S. Li, C.X. Tan, An efficient and convenient method for preparation of disulfides from thiols using air as oxidant catalyzed by Co-salophen, Chin. Chem. Lett. 22 (2011) 1403-1406.
-
[11] L. Xu, J. Cheng, M.L. Trudell, Chromium(VI) oxide catalyzed oxidation of sulfides to sulfones with periodic acid, J. Org. Chem. 68 (2003) 5388-5391.[11] L. Xu, J. Cheng, M.L. Trudell, Chromium(VI) oxide catalyzed oxidation of sulfides to sulfones with periodic acid, J. Org. Chem. 68 (2003) 5388-5391.
-
[12] A. Bordoloi, A. Vinu, S.B. Halligudi, One-step synthesis of SBA-15 containing tungsten oxide nanoclusters: a chemoselective catalyst for oxidation of sulfides to sulfoxides under ambient conditions, Chem. Commun. 45 (2007) 4806-4808.[12] A. Bordoloi, A. Vinu, S.B. Halligudi, One-step synthesis of SBA-15 containing tungsten oxide nanoclusters: a chemoselective catalyst for oxidation of sulfides to sulfoxides under ambient conditions, Chem. Commun. 45 (2007) 4806-4808.
-
[13] I. Gamba, S. Palavicini, E. Monzana, L. Casella, Catalytic sulfoxidation by dinuclear copper complexes, Chem. Eur. J. 15 (2009) 12932-12936.[13] I. Gamba, S. Palavicini, E. Monzana, L. Casella, Catalytic sulfoxidation by dinuclear copper complexes, Chem. Eur. J. 15 (2009) 12932-12936.
-
[14] B. Li, A.H. Liu, L.N. He, et al., Iron-catalyzed selective oxidation of sulfides to sulfoxides with the polyethylene glycol/O2 system, Green Chem. 14 (2012) 130-135.[14] B. Li, A.H. Liu, L.N. He, et al., Iron-catalyzed selective oxidation of sulfides to sulfoxides with the polyethylene glycol/O2 system, Green Chem. 14 (2012) 130-135.
-
[15] (a) J. Legros, C. Bolm, Iron-catalyzed asymmetric sulfide oxidation with aqueous hydrogen peroxide, Angew. Chem. Int. Ed. 42 (2003) 5487-5489;[15] (a) J. Legros, C. Bolm, Iron-catalyzed asymmetric sulfide oxidation with aqueous hydrogen peroxide, Angew. Chem. Int. Ed. 42 (2003) 5487-5489;
-
[20]
(b) J. Legros, C. Bolm, Investigations on the iron-catalyzed asymmetric sulfide oxidation, Chem. Eur. J. 11 (2005) 1086-1092;(b) J. Legros, C. Bolm, Investigations on the iron-catalyzed asymmetric sulfide oxidation, Chem. Eur. J. 11 (2005) 1086-1092;
-
[21]
(c) J. Legros, C. Bolm, Highly enantioselective iron-catalyzed sulfide oxidation with aqueous hydrogen peroxide under simple reaction conditions, Angew. Chem. Int. Ed. 43 (2004) 4225-4228.(c) J. Legros, C. Bolm, Highly enantioselective iron-catalyzed sulfide oxidation with aqueous hydrogen peroxide under simple reaction conditions, Angew. Chem. Int. Ed. 43 (2004) 4225-4228.
-
[16] (a) H. Egami, T. Katsuki, Fe(salan)-catalyzed asymmetric oxidation of sulfides with hydrogen peroxide in water, J. Am. Chem. Soc. 129 (2007) 8940-8941;[16] (a) H. Egami, T. Katsuki, Fe(salan)-catalyzed asymmetric oxidation of sulfides with hydrogen peroxide in water, J. Am. Chem. Soc. 129 (2007) 8940-8941;
-
[23]
(b) H. Egami, T. Katsuki, Optimization of asymmetric oxidation of sulfides with the Fe(salan) complex in water and the expanded scope of its application, Synlett 2008 (2008) 1543-1546.(b) H. Egami, T. Katsuki, Optimization of asymmetric oxidation of sulfides with the Fe(salan) complex in water and the expanded scope of its application, Synlett 2008 (2008) 1543-1546.
-
[17] (a) O.W.J.S. Rutten, A. van Sandwijk, G. van Weert, The electrochemical reduction of nitrate in acidic nitrate solutions, J. Appl. Electrochem. 29 (1999) 87-92;[17] (a) O.W.J.S. Rutten, A. van Sandwijk, G. van Weert, The electrochemical reduction of nitrate in acidic nitrate solutions, J. Appl. Electrochem. 29 (1999) 87-92;
-
[25]
(b) I.M. Kolthoff, M.K. Chantooni, Dissociation constant, Ka, and stability constant K(HA2 ), of the 1:1 homoconjugate of sulfuric and nitric acids in acetonitrile at 298.1 K. Revised values, J. Chem. Eng. Data 44 (1999) 124-129.(b) I.M. Kolthoff, M.K. Chantooni, Dissociation constant, Ka, and stability constant K(HA2 ), of the 1:1 homoconjugate of sulfuric and nitric acids in acetonitrile at 298.1 K. Revised values, J. Chem. Eng. Data 44 (1999) 124-129.
-
[18] L.I. Rossi, S.E. Martín, Possible role of nitrate/nitrite redox cycles in catalytic and selective sulfoxidation reaction Metallic nitrates and bromides as redox mediators: a comparative study, Appl. Catal. A: Gen. 250 (2003) 271-278.[18] L.I. Rossi, S.E. Martín, Possible role of nitrate/nitrite redox cycles in catalytic and selective sulfoxidation reaction Metallic nitrates and bromides as redox mediators: a comparative study, Appl. Catal. A: Gen. 250 (2003) 271-278.
-
[19] (a) I.A. Shuklov, N.V. Dubrovina, A. Bö rner, Fluorinated alcohols as solvents, cosolvents and additives in homogeneous catalysis, Synthesis 19 (2007) 2925-2943;[19] (a) I.A. Shuklov, N.V. Dubrovina, A. Bö rner, Fluorinated alcohols as solvents, cosolvents and additives in homogeneous catalysis, Synthesis 19 (2007) 2925-2943;
-
[28]
(b) K.S. Ravikumar, V. Kesavan, B. Crousse, et al., Mild and selective oxidation of sulfur compounds in trifluoroethanol: diphenyl disulfide and methyl phenyl sulfoxide [(disulfide, diphenyl- and benzene (methylsulfinyl)-)], Org. Synth. 80 (2003) 184-189.(b) K.S. Ravikumar, V. Kesavan, B. Crousse, et al., Mild and selective oxidation of sulfur compounds in trifluoroethanol: diphenyl disulfide and methyl phenyl sulfoxide [(disulfide, diphenyl- and benzene (methylsulfinyl)-)], Org. Synth. 80 (2003) 184-189.
-
-

计量
- PDF下载量: 0
- 文章访问数: 879
- HTML全文浏览量: 4