Trichloroisocyanuric Acid/KBr as a Catalytic System for the Chemoselective Oxidation of Benzylic and Secondary Alcohols

Zolfigol, Mohammad Ali; Shirini, Farhad; Choghamarani, Arash Ghorbani

doi:10.1055/s-2006-942396

Cited by 46 publications

(17 citation statements)

References 12 publications

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“…A plausible mechanism of this oxidation is shown in Scheme V based on reported pathway in literatures, 35,39 our observations, and the obtained results. In summary, we report an efficient method for the selective oxidation of sulfides to sulfoxides under mild and heterogeneous conditions with good to high yields.…”

supporting

confidence: 72%

Aluminium Nitrate/Silica Sulfuric Acid/Bromide Ion: As an Effective and Catalytic Oxidizing Media for the Selective Oxidation of Sulfides to Sulfoxides

Ghorbani‐Choghamarani

Goudarziafshar

Hajjami

et al. 2008

J Chinese Chemical Soc

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Various types of sulfides are chemoselectively oxidized to the corresponding sulfoxides by treatment of Al(NO 3 ) 3 .9H 2 O, silica sulfuric acid and a catalytic amount of NaBr in the presence of wet SiO 2 (50% w/w) in CH 2 Cl 2 at room temperature. The catalytic oxidation procedure is very simple and the products are easily isolated in good yields.Keywords: Sulfides; Sulfoxides; Homoselectivity; Aluminium nitrate; Silica sulfuric acid.The design and development of heterogeneous catalysts are one of the most important objectives in the current area of research interest. The Important aspect of clean technology is the use of environmentally friendly catalysts.1 Recently, the development of efficient and new catalytic systems for various organic transformations is an active ongoing research area and the scope for further improvement towards milder reaction conditions. 2The chemistry of sulfoxides has been attractive to organic chemists. Because sulfoxides are valuable synthetic intermediates for the construction of chemically and biologically important significant molecules.3-5 Sulfoxides have also been used extensively in organic synthesis such as C-C bond-forming, molecular rearrangements and functional group transformations. 6-10 Although various oxidizing agents are used for this purpose, 11-32 unfortunately, some of these reagents are not satisfactory for the selective oxidation of sulfides to the sulfoxides because of several reasons. The first reason is that sulfoxides can undergo overoxidation to sulfones and therefore it is important that the catalyst has low reactivity towards the sulfoxides. Other serious obstacles of the previous procedures are long reaction time, low selectivity, low yields of products, toxicity, and expensive reagents. In continuation of our recent studies on the oxidation reactions, [33][34][35][36][37][38][39] we have been enthusiastic to introduce a new catalytic media, based on in situ generation of X + using aluminium nitrate {Al(NO 3 ) 3 .9H 2 O}, silica sulfuric acid {SiO 2 -OSO 3 H} and a metal halide. Silica sulfuric acid can be easily prepared by the reaction of chlorosulfonic acid with silica gel (Scheme I). 40To find the best reaction conditions for the oxidation of sulfides, a combination of Al(NO 3 ) 3 .9H 2 O, silica sulfuric acid and catalytic amounts of a metal halide (MX) in the presence of wet SiO 2 (50% w/w) in dichloromethane at room temperature was examined for the oxidation of benzyl phenyl sulfide as a model reaction, and the results are summarized in Table 1. As can be seen from Table 1, the best result is referred to Al(NO 3 ) 3 .9H 2 O, silica sulfuric acid and wet SiO 2 (50% w/w) in the presence of catalytic amount of NaBr.Consequently, we presented a new heterogeneous catalytic protocol for the selective oxidation of different types of sulfides 1 to the corresponding sulfoxides 2 using combination of Al(NO 3 ) 3 .9H 2 O I, silica sulfuric acid II and wet SiO 2 (50% w/w) in the presence of catalytic amounts of NaBr IV in dichloromethane at room temperature ...

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confidence: 72%

Aluminium Nitrate/Silica Sulfuric Acid/Bromide Ion: As an Effective and Catalytic Oxidizing Media for the Selective Oxidation of Sulfides to Sulfoxides

Ghorbani‐Choghamarani

Goudarziafshar

Hajjami

et al. 2008

J Chinese Chemical Soc

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“…A suggested mechanism of this oxidation is outlined in Scheme 5 based on our previously reported papers, 7,8,10,21,22 our observations and obtained results.…”

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confidence: 53%

“…In continuation of our recent studies on the application of new reagents on the organic transformations, [17][18][19][20][21][22] we became interested to introduce in a new heterogeneous media for the oxidative coupling of thiols by treating aluminum nitrate nine hydrate (Al(NO3)3․9H2O) and silica sulfuric acid (SiO2-OSO 3 H) in dichloromethane as solvent at room temperature.…”

mentioning

confidence: 99%

An Efficient and New Method on the Oxidative Coupling of Thiols under Mild and Heterogeneous Conditions

Ghorbani‐Choghamarani¹,

Nikoorazm²,

Goudarziafshar³

et al. 2009

Bulletin of the Korean Chemical Society

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“…In continuation of our studies on the application of new oxidizing reagents in the organic transformations [33][34][35][36][37][38], we became interested in the use of a novel oxidizing system, based on the in situ generation of X + , for the selective oxidation of sulfides to sulfoxides.…”

Section: Resultsmentioning

confidence: 99%

Catalytic oxidation of sulfides to sulfoxides using aluminium hydrogen sulfate, sodium nitrite and catalytic amounts of metal bromide

Ghorbani‐Choghamarani

Zeinivand

2010

JICS

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Trichloroisocyanuric Acid/KBr as a Catalytic System for the Chemoselective Oxidation of Benzylic and Secondary Alcohols

Abstract: Chemoselective oxidation of benzylic and secondary alcohols were proceeded by using a catalytic amount of KBr in the presence of trichloroisocyanuric acid and wet SiO 2 under mild and heterogeneous conditions with excellent yields.

Cited by 46 publications

References 12 publications

Aluminium Nitrate/Silica Sulfuric Acid/Bromide Ion: As an Effective and Catalytic Oxidizing Media for the Selective Oxidation of Sulfides to Sulfoxides

Aluminium Nitrate/Silica Sulfuric Acid/Bromide Ion: As an Effective and Catalytic Oxidizing Media for the Selective Oxidation of Sulfides to Sulfoxides

An Efficient and New Method on the Oxidative Coupling of Thiols under Mild and Heterogeneous Conditions

Catalytic oxidation of sulfides to sulfoxides using aluminium hydrogen sulfate, sodium nitrite and catalytic amounts of metal bromide

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