Oxidation of Organic Sulfides by Br2 and H2O2. Electrophilic and Free-Radical Processes

Bravo, Anna; Dordi, Barbara; Fontana, Francesca; Minisci, Francesco

doi:10.1021/jo0017178

Cited by 44 publications

(26 citation statements)

References 7 publications

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“…[12,13] Several catalytic systems have been reported to be active in the oxidation of sulfides. These range from metal-containing [14][15][16][17][18][19][20] and metal-free protocols [21][22][23] to biocatalysts [15] using various oxidants including H 2 O 2 and O 2 .…”

Section: Introductionmentioning

confidence: 99%

Efficient and Highly Selective Aqueous Oxidation of Sulfides to Sulfoxides at Room Temperature Catalysed by Supported Iron Oxide Nanoparticles on SBA‐15

et al. 2011

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The present manuscript describes a simple, efficient and environmentally friendly room temperature aqueous catalytic approach to the selective preparation of sulfoxides from sulfides utilising lowloaded supported iron oxide nanoparticles and aqueous hydrogen peroxide as oxidant. Materials could be easily recovered from the reaction mixture and reused ten times without any loss in activity and no metal leaching was observed during the reaction. This is thus the first selective aqueous oxidation of sulfides using an iron-based heterogeneous system.

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Section: Introductionmentioning

confidence: 99%

Efficient and Highly Selective Aqueous Oxidation of Sulfides to Sulfoxides at Room Temperature Catalysed by Supported Iron Oxide Nanoparticles on SBA‐15

et al. 2011

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“…Efficient oxidation of benzylic sulfides to the corresponding sulfoxides, without C-S bond cleavage, also showed the usefulness of the protocol (Table 1, entries 12,13,14). The latter result is clearly in sharp contrast to those obtained from the BrT catalyzed protocol [32]. Another feature of this protocol was further seen in the selective oxidation of allyl phenyl sulfide to the corresponding sulfoxide.…”

Section: Resultsmentioning

confidence: 83%

“…Although, many of these methods are quite useful, there still remains much room for improvements especially in the case of the selectivity of the reactions. Recently, it has been shown that bromine could be an effective catalyst for oxidation of a variety of sulfides in the presence of 30 % hydrogen peroxide, through a bi-phasic system [32]. It was shown that in this process, either an electrophilic or a free radical mechanism is involved.…”

Section: Introductionmentioning

confidence: 99%

Selective, metal-free oxidation of sulfides to sulfoxides Using 30% hydrogen peroxide catalyzed with N-bromosuccinimide (NBS) under neutral buffered reaction conditions

Karimi

Zareyee

2008

JICS

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This paper is dedicated to Professor Habib Firouzabadi on the occasion of his 65 th birthday and also his retirement Various types of aromatic and aliphatic sulfides are selectively oxidized to the corresponding sulfoxides in good to excellent yields using 30% H 2 0 2 in the presence of catalytic amounts of N-bromosuccinimide (NBS) in buffered aqueous acetonitrile solution (pH =7.00). The results showed that acid sensitive functional groups such as double bonds, and O,O-acetals remained intact under the described reaction conditions

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“…M. Tarasiuk et al the first and second cases, we observed starting material, but in the third sulfoxide 8 with carbonyl group protected by dimethyl ketal. Under reaction condition, bromine is a catalyst of oxidation of sulfide fragment and molecular oxygen is an oxidant [21,22]. The process of ketalization was caused by catalytic amount of HBr in reaction mixture.…”

Section: Methodsmentioning

confidence: 99%

Novel synthesis of 2H-1,5-benzoxathiepin-3(4H)-one and 5H-4,1-benzoxathiepin-3(2H)-one derivatives and chemical properties evaluation

et al. 2015

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New methods for the synthesis of 2H-1,5-benzoxathiepin-3(4H)-one and 5H-4,1-benzoxathiepin-3(2H)-one derivatives have been developed. Carbonyl group of 2H-1,5-benzoxathiepin-3(4H)-one has been protected by cyclic and acyclic ketals. Interaction of 2H-1,5-benzoxathiepin-3(4H)-one with NaBH 4 , hydroxylamine, hydrazines, and Br 2 has been investigated. Strecker reaction has been carried out for the synthesis of corresponding a-amino acid. Combination of Horner-WadsworthEmmons and Michael reactions allowed to obtain derivatives of b-substituted carboxylic acid. Also, 2H-1,5-benzoxathiepin-3(4H)-one have been involved in JohnsonCorey-Chaykovsky reaction. Graphical abstract

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Oxidation of Organic Sulfides by Br₂ and H₂O₂. Electrophilic and Free-Radical Processes

Cited by 44 publications

References 7 publications

Efficient and Highly Selective Aqueous Oxidation of Sulfides to Sulfoxides at Room Temperature Catalysed by Supported Iron Oxide Nanoparticles on SBA‐15

Efficient and Highly Selective Aqueous Oxidation of Sulfides to Sulfoxides at Room Temperature Catalysed by Supported Iron Oxide Nanoparticles on SBA‐15

Selective, metal-free oxidation of sulfides to sulfoxides Using 30% hydrogen peroxide catalyzed with N-bromosuccinimide (NBS) under neutral buffered reaction conditions

Novel synthesis of 2H-1,5-benzoxathiepin-3(4H)-one and 5H-4,1-benzoxathiepin-3(2H)-one derivatives and chemical properties evaluation

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