1122-91-4Relevant articles and documents
Regioselective radical aminofluorination of styrenes
Zhang, Hongwei,Song, Yongcheng,Zhao, Jinbo,Zhang, Jingping,Zhang, Qian
, p. 11079 - 11083 (2014)
The copper-catalyzed radical aminofluorination of styrenes with N-fluorobenzenesulfonimide (NFSI) is realized with high regioselectivity thus affording aminofluorination products with regioselectivities opposite that of the palladium-catalyzed and noncatalyzed processes. Preliminary mechanistic studies suggested the reaction went through a radical pathway and was supported by DFT calculations. In these reactions NFSI is utilized as both a radical nitrogen source and radical fluorine source thus rendering it an attractive reagent.
A mild and efficient method for the oxidation of benzylic alcohols by two-phase electrolysis
Raju, Thasan,Manivasagan, Sankar,Revathy, Balachandran,Kulangiappar, Kumarasamy,Muthukumaran, Arunachalam
, p. 3681 - 3684 (2007)
Electrochemical oxidation of benzylic and substituted benzylic alcohols by two-phase electrolysis yields the corresponding aldehydes as products. The reaction was carried out in a single compartment cell with platinum electrodes at room temperature in chloroform using an aqueous sodium bromide solution (25%) containing a catalytic amount of HBr. The two-phase electrolysis resulted in high yields (74-96%) of benzaldehyde from primary alcohols and secondary alcohols were oxidized to the corresponding ketone but only in low yields under these conditions.
Zinc Bismuthate Zn(BiO3)2. I. A Useful Oxidizing Agent for the Efficient Oxidation of Organic Compounds
Firouzabadi, Habib,Mohammadpour-Baltork, Iraj
, p. 1131 - 1134 (1992)
Zinc bismuthate is an easily prepared and a stable compound.It could be used as an oxidant in organic solvents under aprotic or in the presence of a catalytic amount of a protic solvent.Primary and secondary saturated, allylic, and benzylic alcohols are converted to their carbonyl compounds in high yields.Mildness of the reagent is shown by the oxidation of thiols to their disulfides in excellent yields.Thioethers are also oxidized to their corresponding sulfoxides in good yields.
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Huggins,Yokley
, p. 1160 (1942)
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Cerium-Complex-Catalyzed Oxidation of Arylmethanols under Atmospheric Pressure of Dioxygen and Its Mechanism through a Side-On μ-Peroxo Dicerium(IV) Complex
Paul, Mitali,Shirase, Satoru,Morimoto, Yuma,Mathey, Laurent,Murugesapandian, Balasubramanian,Tanaka, Shinji,Itoh, Shinobu,Tsurugi, Hayato,Mashima, Kazushi
, p. 4008 - 4014 (2016)
A new CeIV complex [Ce{NH(CH2CH2N=CHC6H2-3,5-(tBu)2-2-O)2}(NO3)2] (1), bearing a dianionic pentadentate ligand with an N3O2 donor set, has been prepared by treating (NH4)2Ce(NO3)6 with the sodium salt of ligand L1. Complex 1 in the presence of TEMPO and 4 ? molecular sieves (MS4 A) has been found to serve as a catalyst for the oxidation of arylmethanols using dioxygen as an oxidant. We propose an oxidation mechanism based on the isolation and reactivity study of a trivalent cerium complex [Ce{NH(CH2CH2N=CHC6H2-3,5-(tBu)2-2-O)2}(NO3)(THF)] (2), its side-on μ-O2 adduct [Ce{NH(CH2CH2N=CHC6H2-3,5-(tBu)2-2-O)2}(NO3)]2(μ-η2:η2-O2) (3), and the hydroxo-bridged CeIV complex [Ce{NH(CH2CH2N=CHC6H2-3,5-(tBu)2-2-O)2}(NO3)]2(μ-OH)2 (4) as key intermediates during the catalytic cycle. Complex 2 was synthesized by reduction of 1 with 2,5-dimethyl-1,4-bis(trimethylsilyl)-1,4-diazacyclohexadiene. Bubbling O2 into a solution of 2 resulted in formation of the peroxo complex 3. This provides the first direct evidence for cerium-catalyzed oxidation of alcohols under an O2 atmosphere. Cerium-catalyzed alcohol oxidation: A new CeIV complex [Ce{NH(CH2CH2N=CHC6H2-3,5-(tBu)2-2-O)2}(NO3)2] (1) has been shown to serve as a catalyst for the oxidation of arylmethanols using dioxygen as an oxidant in the presence of TEMPO and molecular sieves MS4 A (see scheme). CeIII complex 2, obtained by reduction of 1 with 2,5-dimethyl-1,4-bis(trimethylsilyl)-1,4-diazacyclohexadiene, reacted with O2 to give the peroxo complex 3. This provides the first direct evidence for operation of the peroxo mechanism in the cerium-catalyzed oxidation of alcohols under O2 atmosphere.
Synthetic utility of iodic acid in the oxidation of benzylic alcohols to aromatic aldehydes and ketones
Imai, Sho,Togo, Hideo
, p. 6948 - 6954 (2016)
Various primary and secondary benzylic alcohols were efficiently oxidized to aromatic aldehydes and aromatic ketones with iodic acid in DMF at 60?°C for 2?h and with iodic acid in the presence of TEMPO (5?mol?%) in DMF at room temperature, respectively. The former method was effective for the oxidation of sterically hindered alcohols at 60?°C and the latter method was effective for the oxidation of less sterically hindered alcohols at room temperature.
gem-Difluorination of 2,2-diaryl-1,3-dithiolanes by Selectfluor and pyridinium polyhydrogen fluoride
Reddy, V. Prakash,Alleti, Ramesh,Perambuduru, Meher K.,Welz-Biermann, Urs,Buchholz, Herwig,Prakash, G. K. Surya
, p. 654 - 656 (2005)
2,2-Diaryl-1,3-dithiolanes, readily obtainable from diaryl ketones, were transformed into the corresponding gem-difluoro compounds using a novel reagent combination involving Selectfluor and pyridinium polyhydrogen fluoride (PPHF) under mild conditions in moderate to good yields. The Royal Society of Chemistry 2005.
"Click Chemistry" Mediated Functional Microporous Organic Nanotube Networks for Heterogeneous Catalysis
Yu, Wei,Zhou, Minghong,Wang, Tianqi,He, Zidong,Shi, Buyin,Xu, Yang,Huang, Kun
, p. 5776 - 5779 (2017)
The synthesis of azide functional microporous organic nanotube networks (N3-MONNs) via a Friedel-Crafts hyper-cross-linking reaction is reported. Subsequently, a general method for obtaining heterogeneous catalysts through a Cu-catalyzed alkyne-azide reaction is presented. The small-molecule catalysts such as 2,2,6,6,-tetramethylpiperidine-1-oyl and 4-(N,N-dimethylamino)pyridine can be anchored into the MONNs. Owing to the hierarchically porous structure and high surface area, these catalysts show high activity in selective oxidation of alcohols and acylation reaction, respectively.
Competing bromination and oxidation pathways in acid bromate solutions: An experimental and theoretical study
Rothenberg, Gadi,Beadnall, Richard M.H.,McGrady, John E.,Clark, James H.
, p. 630 - 635 (2002)
The qualities that render concentrated H2SO4-BrO3 mixtures as powerful bromination and oxidation reagents are examined by following the reactions of acetophenone, cyclohexanol and benzaldehyde, and by using density functio
{-N+(CH3)2CH2CH 2N+[(CH3)2](CH2) 4-}n S2O82-: A selective and recyclable reagent for oxidation of alcohols and hydroquinones in water
Tajbakhsh, Mahmood,Lakouraj, Moslem Mansour,Ramzanian-Lehmali, Farhad
, p. 1724 - 1728 (2006)
This article describes the oxidation of alcohols and hydroquinones in water using polymer-supported peroxodisulfate, which has been prepared by mixing an aqueous solution of 2,4-ionene with an aqueous solution of potassium peroxodisulfate at room temperature. Georg Thieme Verlag Stuttgart.
Mesityltriphenylbismuthonium tetrafluoroborate as an efficient bismuth(V) oxidant: remarkable steric effects on reaction rates and chemoselectivities in alcohol oxidation
Matano, Yoshihiro,Suzuki, Takeshi,Shinokura, Tomonori,Imahori, Hiroshi
, p. 2885 - 2888 (2007)
In the presence of N,N,N′,N′-tetramethylguanidine, mesityltriphenylbismuthonium tetrafluoroborate oxidizes primary and secondary alcohols to aldehydes and ketones, respectively, under mild conditions. In this reaction, the mesityl ligand exclusively abstracts an α-hydrogen to afford mesitylene and triphenylbismuthane as side products. A remarkable steric effect has also been exhibited in the chemoselective oxidation between primary and secondary alcohols.
Mild oxidation of benzylic amines into aldehydes using an oxidative Polonovski-like process
Desjardins, Samuel,Jacquemot, Guillaume,Canesi, Sylvain
, p. 1497 - 1500 (2012)
A chemoselective and environmentally benign oxidation of benzylic amines into aldehydes mediated by a hypervalent iodine reagent has been developed. This mild oxidative version of the Polonovski process may be selectively carried out in the presence of several functionalities including a free alcohol and provides new synthetic opportunities as a masked aldehyde segment. Georg Thieme Verlag Stuttgart · New York.
Rapid and selective oxidation of benzyl alcohols to aldehydes and ketones with novel vanadium polyoxometalate under solvent-free conditions
Dewan, Anindita,Sarma, Tridib,Bora, Utpal,Kakati, Dilip K.
, p. 2563 - 2565 (2011)
A novel vanadium polyoxometalate [(C6H5CH 2)(CH3)3N]3[H3V 10O28]3H2O works as a useful oxidant for selective and rapid oxidation of benzylic alco
Highly atom efficient synthesis of 2,2,4,5-tetrasubstituted 3(2H)-furanones having both hydroxyl and amino substituents
Antony, Jesna,Mathai, Sindhu,Natarajan, Rakesh,P. Musthafa, Sumi,Rappai, John P.,S. Devaky, Karakkattu
supporting information, (2022/02/25)
We have developed a highly atom efficient synthesis of tetrasubstituted 3(2H)-furanones from easily accessible starting materials such as C,N-diarylaldonitrones and dibenzoylacetylene. Control experiments revealed that reaction of aldonitrones having electron-withdrawing groups on the C-aryl substituent in polar aprotic solvents exhibited high product selectivity while reaction temperature has only a negligible effect on product yield and selectivity.
Poly(ethylene glycol) dimethyl ether mediated oxidative scission of aromatic olefins to carbonyl compounds by molecular oxygen
Yu, Tao,Guo, Mingqing,Wen, Simiaomiao,Zhao, Rongrong,Wang, Jinlong,Sun, Yanli,Liu, Qixing,Zhou, Haifeng
, p. 13848 - 13852 (2021/04/22)
A simple, and practical oxidative scission of aromatic olefins to carbonyl compounds using O2as the sole oxidant with poly(ethylene glycol) dimethyl ether as a benign solvent has been developed. A wide range of monosubstituted,gem-disubstituted, 1,2-disubstituted, trisubstituted and tetrasubstituted aromatic olefins was successfully converted into the corresponding aldehydes and ketones in excellent yields even with gram-scale reaction. Some control experiments were also conducted to support a possible reaction pathway.
Method for preparing aldehyde compound through olefin oxidation
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Paragraph 0021-0025, (2021/06/09)
The invention provides a simple synthesis method for preparing an aldehyde compound through olefin oxidation, and the related preparation method is an olefin oxidative cracking reaction in which oxygen participates, and comprises the following specific steps: in the presence of a solvent and an oxidant, performing oxidative cracking on an olefin raw material to prepare a corresponding aldehyde product. Compared with a traditional method, the method does not need to add any catalyst or ligand, does not need to use high-pressure oxygen, has the advantages of simple and mild reaction conditions, environmental protection, low cost, high atom economy and the like, is wide in substrate application range and high in yield, and has wide application prospects in synthesis of aldehyde medical intermediates and chemical raw materials.
