Synthesis of benzophenones from geminal biaryl ethenes using m-chloroperbenzoic acid

Singh, Fateh V.; Milagre, Humberto M. S.; Eberlin, Marcos N.; Stefani, Hélio A.

doi:10.1016/j.tetlet.2009.02.164

Cited by 57 publications

(24 citation statements)

References 46 publications

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“…The cleavage of terminal CC double bonds of geminal biarylethenes was performed employing m ‐chloroperbenzoic acid ( m CPBA) in dichloromethane without the need of any catalyst (Scheme A) 39. Additionally, 2,4‐substituted enynes were converted to the corresponding ynone systems under mild reaction conditions (Scheme B).…”

Section: Alkene Cleavage By Chemical Methodsmentioning

confidence: 99%

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Oxidative Alkene Cleavage by Chemical and Enzymatic Methods

2013

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The cleavage of alkenes to the corresponding carbonyl products is a widely employed method in organic synthesis, especially to introduce oxygen functionalities into molecules, remove protecting groups and tailor large molecules. Chemical methods available for alkene cleavage include, for instance, ozonolysis, several metal-based variants (KMnO 4 , OsO 4 , RuO 4 , etc.), electrochemical alternatives, singlet oxygen, hypervalent iodine and organic molecules in combination with oxygen. Furthermore, several enzymatic methods for alkene cleavage have been described to establish safe, mild and selective oxidation methods. Various heme and non-heme iron-dependent enzymes catalyse the alkene cleavage at ambient temperature and atmospheric pressure in an aqueous buffer, showing good chemo-and regioselectivities in selected cases. Quite recently some Cu-, Mn-and Ni-dependent enzymes have been identified for this reaction. This review gives an overview of the different chemical and enzymatic methods available for the cleavage of alkenes.

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Section: Alkene Cleavage By Chemical Methodsmentioning

confidence: 99%

“…[39] Additionally, 2,4-substituted enynes were converted to the corresponding ynone systems under mild reaction conditions (Scheme 12B). [39] Additionally, 2,4-substituted enynes were converted to the corresponding ynone systems under mild reaction conditions (Scheme 12B).…”

Section: Hypervalent Iodinementioning

confidence: 99%

Oxidative Alkene Cleavage by Chemical and Enzymatic Methods

2013

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“…Unfortunately, ruthenium and osmium are expensive metals, and osmium and chromium are also very toxic, which limits the industrial application of the above-mentioned systems [ 1 ]. Oxone [ 7 , 8 ], PhI(OAc) 2 [ 9 ], m -chloroperoxybenzoic acid [ 10 ], and tert -butyl hydroperoxide [ 11 , 12 , 13 , 14 , 15 ] have also been used as oxidants. Industrial oxidative cleavage reaction of oleic acid to pelargonic and azelaic acids [ 1 ] is carried out using ozone as an oxidizing agent without the addition of a metallic catalyst [ 16 ]; however, due to its instability, ozone is hazardous and requires in situ formation, and it also requires specialized equipment, which increases production costs [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Oxidation of Long-Chain α-Olefins Using Environmentally-Friendly Oxidants

et al. 2020

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Studies on the oxidation of α-olefins via the two-stage method are presented. The new method consisted of oxidizing C30+ α-olefins with hydrogen peroxide (2 equiv.) and subsequent oxidation with oxygen. Products with high acid numbers (29–82 mgKOH/g) and saponification numbers (64–140 mgKOH/g) were obtained and compared with products obtained using only hydrogen peroxide or oxygen. It was demonstrated that H2O2 can be partially replaced by oxygen in the oxidative cleavage reaction of α-olefins. N-hydroxyphthalimide in combination with Co(acac)2 demonstrated high activity in the oxidation stage using oxygen.

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“…The direct oxidative cleavage of olefins is still a challenge and greatly dependent on the use of conventional methods, for instance using ozone [5][6][7][8], KMnO 4 [9,10], oxone [11,12], NaIO 4 [13], OsO 4 [14], high valance I 2 [15,16], m-chloroperbenzoic acid, etc. [17,18]. However, these methods suffer from the long reaction period, over oxidation, low selectivity, limited substrate scope, poor functional group tolerance and environment unfriendliness.…”

Section: Introductionmentioning

confidence: 99%

Quinazolin-4(3H)-ones: A Tangible Synthesis Protocol via an Oxidative Olefin Bond Cleavage Using Metal-Catalyst Free Conditions

Sharif

2020

Applied Sciences

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An efficient and selective oxidative procedure for the synthesis of quinazolinones from readily available o-aminobenzamides and styrenes was developed. A number of potentially pharmacologically relevant quinazolinones were prepared using metal- and catalyst-free conditions. The synthesis procedure highlights the sustainable operation, low-priced, free from perilous materials, green solvent and environmental affability. The synthesized products were isolated in moderate to excellent yields.

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Synthesis of benzophenones from geminal biaryl ethenes using m-chloroperbenzoic acid

Cited by 57 publications

References 46 publications

Oxidative Alkene Cleavage by Chemical and Enzymatic Methods

Oxidative Alkene Cleavage by Chemical and Enzymatic Methods

Oxidation of Long-Chain α-Olefins Using Environmentally-Friendly Oxidants

Quinazolin-4(3H)-ones: A Tangible Synthesis Protocol via an Oxidative Olefin Bond Cleavage Using Metal-Catalyst Free Conditions

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