5779-95-3Relevant academic research and scientific papers
An expeditious and efficient method for the oxidation of benzyl alcohols by homogeneous electrolysis
Jagatheesan, Rathinavel,Shanmugavelan, Poovan,Sambathkumar, Subramaniyan,Ramesh, Pugalenthi
supporting information, p. 3013 - 3022 (2021/08/12)
A greener and inexpensive electrochemical method has been developed for the oxidation of benzyl alcohols by homogeneous electrolysis. The electrochemical reaction was carried out in an undivided cell equipped with carbon and stainless steel electrodes at room temperature. The homogeneous solution made up of acetonitrile/water containing substrate and ammonium bromide with a catalytic amount of H2SO4 as supporting electrolyte. The reaction condition was optimized with various electrochemical experimental parameters and evaluated with various substituted benzyl alcohols to result in excellent yield of aldehydes (>83%).
LIGHT INDUCED CATALYTIC C-H OXYGENATION OF ALKANES
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Paragraph 00219, (2021/04/02)
A method of oxygenating a benzylic C-H bond is provided. The method comprises light induced activation of an initiator and subsequent reaction with oxygen, resulting in the formation of free radicals. Subsequently, free radicals catalyze the reaction of the benzylic C-H bond with oxygen, thereby forming an oxygenated compound.
Ferric ion concentration-controlled aerobic photo-oxidation of benzylic C–H bond with high selectivity and conversion
Bu, Hongzhong,Gu, Jiefan,Li, Yufeng,Ma, Hongfei,Wan, Yuting,Wu, Zheng-Guang,Zhang, Weijian,Zhou, Ying'ao,Zhu, Hongjun
, (2021/07/16)
A Fe(III)-promoted highly selective photo-oxidation of benzylic C–H bond delivering relative carbonyl products is reported. By altering the concentration of ferric salt, methylarenes can be selectively oxidized under UV irradiation to furnish aromatic aldehydes or acids, respectively. By this protocol, the oxidation of ethylarenes provides the corresponding acetophenones. The reaction is inferred to involve divergent pathways in different concentrations of catalyst for the alternative selectivity between aldehydes and aicds. The reusable catalyst, high conversion and selectivity make this oxidation a green and economic protocol for the synthesis of aromatic carbonyl compounds.
Visible-Spectrum Solar-Light-Mediated Benzylic C-H Oxygenation Using 9,10-Dibromoanthracene As an Initiator
Santra, Sourav K.,Szpilman, Alex M.
, p. 1164 - 1171 (2020/12/23)
We report a visible-light-mediated benzylic C-H oxygenation reaction. The reaction is initiated by solar light or the blue LED activation of 9,10-dibromoanthracene in a reaction with oxygen and takes place at ambient temperature and air pressure. Secondary benzylic positions are oxygenated to ketones, while tertiary benzylic carbons are oxygenated to give hydroperoxides. Notably, cumene hydroperoxide is produced in a higher yield and at milder conditions than the currently employed industrial conditions.
Metal- And additive-free C-H oxygenation of alkylarenes by visible-light photoredox catalysis
García Manche?o, Olga,Kuhlmann, Jan H.,Pérez-Aguilar, María Carmen,Piekarski, Dariusz G.,Uygur, Mustafa
supporting information, p. 3392 - 3399 (2021/05/21)
A metal- and additive-free methodology for the highly selective, photocatalyzed C-H oxygenation of alkylarenes under air to the corresponding carbonyls is presented. The process is catalyzed by an imide-acridinium that forms an extremely strong photooxidant upon visible light irradiation, which is able to activate inert alkylarenes such as toluene. Hence, this is an easy to perform, sustainable and environmentally friendly oxidation that provides valuable carbonyls from abundant, readily available compounds.
Reaction method for selectively synthesizing aromatic aldehyde or aromatic carboxylic acid
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Paragraph 0033-0034, (2020/12/05)
The invention provides a reaction method for selectively synthesizing aromatic aldehyde or aromatic carboxylic acid. Toluene aromatic hydrocarbon without substituent or with substituent on a benzene ring is used as a raw material, an inorganic salt of ferric iron is used as a catalyst, air or oxygen is used as an oxidizing agent, a mixed solution of acetonitrile and water is used as a solvent, theraw material is oxidized by adjusting the dosage of the catalyst to obtain aromatic aldehyde or aromatic carboxylic acid, and the aromatic aldehyde or aromatic carboxylic acid is irradiated by ultraviolet light for 10-16 hours. Aromatic carboxylic acid obtained under the condition that the dosage of the catalyst is 5-50% mol of aromatic hydrocarbon is used as a main product, wherein the use amount of the catalyst is 70-200% mol of aromatic hydrocarbon. The reaction method provided by the invention has the characteristics of atom economy and high selectivity, uses the metal iron salt with richearth content for catalysis, and has the advantages of mild conditions, recyclable catalyst and solvent and the like.
Clean Ar-Me conversion to Ar-aldehyde with the aid of carefully designed metallocorrole photocatalysts
Chen, Qiu-Cheng,Churchill, David G.,Fite, Shachar,Gross, Zeev,Kolanu, Sudhakar,Lee, Woohyun,Zhan, Xuan
, p. 996 - 1000 (2020/08/28)
Toluene, p-xylene and mesitylene were cleanly converted to their corresponding monoaldehydes via mild photooxygenation utilizing transition metal and main group β-CF3-substituted corroles. Aldehyde yield increased as more electron-donating CH3 groups are present on the substrate. 4-P was most efficient (TON ～ 1072, mesitylene) via the singlet oxygen vis the superoxide mechanism.
Method for reducing carboxylic acid into aldehyde compounds
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Paragraph 0047-0050, (2020/02/27)
The invention discloses a method for reducing carboxylic acid into aldehyde compounds, and belongs to the field of organic chemical synthesis. Specifically, in an argon atmosphere, a carboxylic acid compound, a transition metal nickel compound, an anhydride compound, a ligand and a reducing agent are dissolved in an organic solvent, the mixture is heated and subjected to stirring reaction, after the reaction is finished, the pressure is reduced to remove the organic solvent, column chromatography separation is performed, and various aldehyde compounds are obtained. The method has the advantages of simple synthesis steps, mild reaction conditions, simplicity and easiness in operation, realization of successful reduction of the carboxylic acid compound into the aldehyde organic compounds, small use amount of the reaction catalyst, high product yield, and provision of a new approach for reduction of the carboxylic acid compound into the aldehyde compounds. Compared with a conventional method, the method has the advantages that raw materials are cheap, easy to obtain and environmentally friendly, substrate universality and functional group compatibility are improved, and the method hascertain innovativeness and unique research significance in organic synthesis methodology.
Benzylation of Arenes with Benzyl Halides under Promoter-Free and Additive-Free Conditions
Cheng, Xinqiang,Shan, Jiankai,Tian, Xinshe,Ren, Yun-Lai,Zhu, Yanyan
, p. 4404 - 4410 (2019/07/03)
It was found that benzyl chlorides and bromides could directly react with electron-rich arenes, which provided an example of promoter-free and additive-free benzylation of arenes. A variety of benzyl chlorides and bromides were treated with benzene rings to give the targeted products in low to high yields. The present conditions tolerated the vinyl group of the substrates. Preliminary mechanistic investigation suggests that the present reactions possibly proceed via an autocatalytic mechanism pathway.
Efficient acceptorless photo-dehydrogenation of alcohols and: N -heterocycles with binuclear platinum(ii) diphosphite complexes
Zhong, Jian-Ji,To, Wai-Pong,Liu, Yungen,Lu, Wei,Che, Chi-Ming
, p. 4883 - 4889 (2019/05/16)
Although photoredox catalysis employing Ru(ii) and Ir(iii) complexes as photocatalysts has emerged as a versatile tool for oxidative C-H functionalization under mild conditions, the need for additional reagents acting as electron donor/scavenger for completing the catalytic cycle undermines the practicability of this approach. Herein we demonstrate that photo-induced oxidative C-H functionalization can be catalysed with high product yields under oxygen-free and acceptorless conditions via inner-sphere atom abstraction by binuclear platinum(ii) diphosphite complexes. Both alcohols (51 examples), particularly the aliphatic ones, and saturated N-heterocycles (24 examples) can be efficiently dehydrogenated under light irradiation at room temperature. Regeneration of the photocatalyst by means of reductive elimination of dihydrogen from the in situ formed platinum(iii)-hydride species represents an alternative paradigm to the current approach in photoredox catalysis.
