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Construction of diaminobenzoquinone imines via ferrocene-initiated radical reaction of benzoquinone with amines

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Chinese Chemical Letters 2020年第3期31卷 733-735页

作者： Yadong Feng Ying Liu Qi Fu Zhongai Zou Jinhai Shen Xiuling Cui College of Environment and Public Health Xiamen Huaxia UniversityXiamen 361024China Engineering Research Center of Molecular Medicine of Ministry of Education Key Laboratory of Fujian Molecular MedicineKey Laboratory of Xiamen Marine and Gene DrugsSchool of Biomedical SciencesHuaqiao UniversityXiamen 361021China

A ferrocene-initiated radical reaction of benzoquinone with amines has been successfully developed for the direct access to diaminobenzoquinone imines in high yields,in which the comme rcially available and cheap ferrocene was employed as a radical initiator and TBHP was used as an oxidant.Moreover,this reaction could be achieved with low loading of ferrocene(0.5 mol%).This protocol is highly efficient with good substrate tolera nce and provides a new approach for the construction of benzoquinone imines with potential pharmaceutical interest.

关键词： Benzoquinone imines Ferrocene-initiated Radical process Benzoquinone Amines

Simple manganese carbonyl catalyzed hydrogenation of quinolines and imines

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Chinese Chemical Letters 2020年第7期31卷 1890-1894页

作者： Zelong Wang Lei Chen Guoliang Mao Congyang Wang Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Molecular Recognition and FunctionCAS Research/Education Center for Excellence in Molecular SciencesInstitute of ChemistryChinese Academy of SciencesBeijing 100190China University of Chinese Academy of Sciences Beijing 100049China Provincial Key Laboratory of Oil&Gas Chemical Technology College of Chemistry and Chemical EngineeringNortheast Petroleum UniversityDaqing 163318China Physical Science Laboratory Huairou National Comprehensive Science CenterBeijing 101400China

Manganese-catalyzed hydrogenation of unsaturated molecules has made tremendous progresses recently benefiting from non-innocent pincer or bidentate ligands for manganese.Herein,we describe the hydrogenation of quinolines and imines catalyzed by simple manganese carbonyls,Mn2(CO)10 or MnBr(CO)5,thus eliminating the prerequisite pincer-type or bidentate ligands.

关键词： Manganese Hydrogenation Quinolines imines Homogeneous catalysis

Direct synthesis of imines by 9-azabicyclo-[3,3,1]nonan-N-oxyl/KOH-catalyzed aerobic oxidative coupling of alcohols and amines

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Chinese Chemical Letters 2018年第8期29卷 1269-1272页

作者： Yan Wan Jia-Qi Ma Chao Hong Mei-Chao Li Li-Qun Jin Xin-Quan Hu Bao-Xiang Hu Wei-Min Mo Nan Sun Zhen-Lu Shen College of Chemical Engineering Zhejiang University of Technology

A simple and efficient method for preparation of imines by the oxidative coupling of benzyl alcohols with aromatic amines or aliphatic amines was developed. The reaction was catalyzed by 9-azabicyclo[3.3.1]nonan-N-oxyl（ABNO）/KOH with air as the economic and green oxidant. Under the optimal reaction conditions, a variety of imines were obtained in 80%-96% isolated yields.

关键词： imines Benzyl alcohols Amines ABNO Air

Selective photosynthesis of imines from biomass-derived aldehydes over Ni/TiO2

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Rare Metals 2024年第3期43卷 1116-1124页

作者： Wu-Lin Li Qing-Qing Zhang Lin Dong Wen-Jun Zhang Li-Li Lin Zu-Peng Chen Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources International Innovation Center for Forest Chemicals and MaterialsCollege of Chemical EngineeringNanjing Forestry University Institute of Industrial Catalysis State Key Laboratory of Green Chemistry Synthesis TechnologyCollege of Chemical EngineeringZhejiang University of Technology

Photocatalytic reductive amination of biomass-derived aldehydes is a desirable way to selectively upgrade biomass into value-added nitrogen-containing chemicals under mild conditions.However,it is challenging to produce imines in high selectivity because of the undesirable side reactions caused by the activity of functional groups.Here,we demonstrate the highly reactive and selective production of imines from biomass derived aldehydes via the photocatalytic reductive amination,using a defective TiO2supported nickel catalyst.The employment of methanol as the hydrogen donor and ammonia solution as the nitrogen source avoids the use of high-pressure H2and expensive amines,rendering the current catalytic process safe,economical,and environmentally friendly.In depth investigations attribute the improved separation and transfer of photogenerated charge carriers to the presence of oxygen vacancies and decorated Ni nanoparticles,thereby accelerating the production of imines from benzaldehyde amination(conversion,95.8%;seleetivity,95.2%).Furthermore,the developed system could be easily translated to the photocatalytic conversions of various biomass derived aldehydes,which provided an example of a cost-effective and sustainable approach for the valorization of biomass derived feedstocks.

关键词： Photocatalysis Biomass derivatives imines Reduction amination Heterogeneous catalyst

Regio-and Diastereoselective Access to 4-Imidazolidinones via an Aza-Mannich Initiated Cyclization of Sulfamate-Derived Cyclic imines with α-Halo Hydroxamates

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Regio-and Diastereoselective Access to 4-Imidazolidinones vi...

Palladium-or Copper-Catalyzed Aerobic Oxidative Synthesis of imines from Alcohols and Amines under Ambient Conditions

中国化学会·第十六届全国有机合成化学学术研讨会

作者： Jing Zhou Ya-Li Qu 陈亚静 School of Pharmaceutical Sciences Zhengzhou University 郑州大学

An efficient regio-and diastereoselective cyclization of sulfamate-derived cyclic imines with unsubstituted or mono substituted α-halo hydroxamates is developed under mild conditions.This reaction proceeds smoothly under transition-metal free conditions via a domino aza-Mannich addition/intramolecular nucleophilic substitution sequence,providing a convenient route to access 2-monosubstituted and 2,5-disubstituted 4-imidazolidinones.Notably,the products were obtained with single trans-isomers in moderate to excellent yields.

关键词： 4-imidazolidinones imines α-halo hydroxamates [3+2] cyclization

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Palladium-or Copper-Catalyzed Aerobic Oxidative Synthesis of...

Bidirectional role of synthetic musk tonalide as photosensitizer and activator on amino acids:Formation of sensitizer imine at aqueous chemistry interface of skin

中国化学会第28届学术年会

作者： Haiwen Tian,Lan Jiang,Xiaochun Yu and Qing Xu* College of Chemistry and Materials Engineering,Wenzhou University,Wenzhou 325035

＜正＞imines are a class of nitrogen compounds of high significance in chemistry.For the high reactivity of the C=N double bond,they are both important nitrogen sources and key intermediates in various types of transformations. Therefore,synthesis and applications of imines are essentially the ever-appealing topics in chemistry.However, challenges still remain in the academic researches. Despite other progresses for imine synthesis,traditional condensation of aldehydes or ketones with amines is most often the method of choice.1 Since aldehydes and

关键词： imines Alcohols Amines Aerobic Oxidative Reaction Pd or Cu catalysis

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Eco-Environment & Health 2023年第1期2卷 32-39页

作者： Na Luo Yanpeng Gao Mei Wang Xiaolin Niu Guiying Li Taicheng An Guangdong-Hong Kong-Macao Joint Laboratory for Contaminants Exposure and Health Guangdong Key Laboratory of Environmental Catalysis and Health Risk ControlInstitute of Environmental Health and Pollution ControlGuangdong University of TechnologyGuangzhou 510006China Guangzhou Key Laboratory of Environmental Catalysis and Pollution Control Key Laboratory of City Cluster Environmental Safety and Green Development of the Ministry of EducationSchool of Environmental Science and EngineeringGuangdong University of TechnologyGuangzhou 510006China

Personal care products(PCPs)inevitably come into contact with the skin in people’s daily life,potentially causing adverse effects on human health.The adverse effects can be exacerbated under UV irradiation but are rarely studied.In this study,to clearly understand the damage of representative PCPs to human skin and their photochemical transformation behaviors,fragrance tonalide(AHTN)was measured in the presence of amino acids as a basic building block of human tissue.The results showed that amino acids could decelerate the photochemical transformation rate of AHTN,increasing the likelihood of AHNT persisting on the skin surface and the health risk to the human being.Further,the interaction between amino acids and AHTN was investigated.AHTN could play bidirectional roles in damaging amino acids:the photosensitizer and reactive activator.As a photosensitizer,the ^(1)O_(2) generated from the AHTN photosensitization was partly employed to oxidative damage amino acids.Furthermore,by combining experiments with quantum chemical computation,the carbonyl group of the activator AHTN was found to be the active site to activate the N-containing group of amino acids.The activation mechanism was the electron transfer between AHTN and amino acids.imines formed during the photochemical transformation of AHTN with histidine/glycine were the molecular initiating event for potential skin sensitization.This study reported for the first time that skin photosensitizer formation threatens human health during the photochemical transformation of AHTN.

关键词： Personal care products Amino acids Photosensitive damage Electron transfer imines

Efficient Solvent-Free Preparation of imines, and Their Subsequent Oxidation with <i>m</i>-CPBA to Afford Oxaziridines

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Green and Sustainable Chemistry 2019年第4期9卷 143-154页

作者： Luis álvarez-Santamaría Eusebio Juaristi Alexa Berenice Arroyo-Colín Jorge Palma-Flores Fanny Araceli Cabrera-Rivera Jaime Escalante Centro de Investigaciones Químicas Universidad Autónoma del Estado de Morelos Cuernavaca Morelos Mexico Departamento de Química Centro de Investigación y de Estudios Avanzados Ciudad de México México El Colegio Nacional Luis Gonzáles Obregón 23 Centro Histórico Ciudad de México México

A simple one-pot procedure for the preparation of imines from the corresponding aldehydes and amines, and their subsequent oxidation reaction with m-CPBA to produce synthetically useful oxaziridines is reported. The method is applicable to imines derived from both aliphatic and aromatic aldehydes and diverse alkyl amines. Short reaction times, essentially quantitative yields, very mild reaction conditions, and easy purification are the main features of the procedure reported herein.

关键词： Solvent-Free Reaction imines Oxaziridines Oxidation Reaction m-CPBA

A New Phosphine-Amine-Oxazoline Ligand for Ru-Catalyzed Asymmetric Hydrogenation of N-Phosphinylimines

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Chinese Journal of Chemistry 2018年第12期36卷 1151-1155页

作者： Xiaochen Ma Lin Qiao Guixia Liu Zheng Huang State Key laboratory of Organometallic Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of Sciences345 Lingling RdShanghai 200032China

A series of chiral phosphine‐amine‐oxazoline (PAO) ligands with an NH moiety were synthesized and applied to the ruthenium‐catalyzed asymmetric hydrogenation of N‐phosphinylimines. The ligand bearing phenyl groups at the phosphorus moiety and isopropyl at the oxazoline moiety exhibits good activity and excellent enantioselectivity (up to 99% ee). This catalytic system provides an efficient and mild approach to access enantioriched amines. [ABSTRACT FROM AUTHOR]

关键词： amines chiral ligand hydrogenation imines ruthenium