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Synergistic roles of platinum nanoparticles and sodium ions within beta zeolites in N-alkylation of amines with aromatic alcohols

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中国科学:化学英文版 2023年第9期66卷 2690-2699页

作者： Yue Wu Shibo Xi Cailing Chen Qizhi Hu Zhuo Xiong Jianyue Wang Yihu Dai Yu Han Shi Jiang Jun Wang Yu Zhou State Key Laboratory of Materials-Oriented Chemical Engineering College of Chemical EngineeringNanjing Tech UniversityNanjing 211816China Institute of Sustainability for Chemicals Energy and EnvironmentA*STAR(Agency for ScienceTechnology and Research)Singapore 627833Singapore Advanced Membranes and Porous Materials Center Physical Sciences and Engineering DivisionKing Abdullah University of Science and TechnologyThuwal 23955-6900Saudi Arabia Institute of Advanced Synthesis School of Chemistry and Molecular EngineeringNanjing Tech UniversityNanjing 211816China

N-alkylation of amines with alcohols is a promising green route for the synthesis of N-alkylamines, but the designation of highly active and stable heterogeneous catalysts remains one challenge. In this work, we initiated the application of zeolite-encapsulated noble metal nanoparticles(NPs) in the N-alkylation of amines with aromatic alcohols. Platinum(Pt) NPs were directly confined into the framework of BEA zeolite with tunable Si/Al molar ratios and Na^(+) contents. The champion catalyst afforded the extremely high turnover number(TON) of 6,176 and turnover frequency(TOF) of 3,390 h^(-1) plus stable recyclability and broad substrate compatibility. The Na ions modulated the electronic state of Pt NPs to reach a moderate Pt–H strength, which wellbalanced the two crucial steps of dehydrogenation and H-transfer and accounted for the high catalytic performance. The encapsulation of zeolites provided spatial satisfaction for the synergy effect above and enhanced the stabilization of Pt NPs.

关键词： heterogeneous catalysis zeolite amines N-alkylation nano catalysts

Redox-neutral dehydrogenative cross-coupling ofalcohols and amines enabled by nickel catalysis

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Organic Chemistry Frontiers 2022年第6期9卷 1703-1710页

作者： Zijuan Yan Feipeng Liu Xuchao Wang Qing Qiang Yongjie Li Yao Zhang Zi-Qiang Rong Frontiers Science Center for Flexible Electronics(FSCFE) Shaanxi Institute of Flexible Electronics(SIFE)&Shaanxi Institute of Biomedical Materials and Engineering(SIBME)Northwestern Polytechnical University(NPU)127 West Youyi RoadXi’an 710072P.R.China College of Chemistry Liaoning UniversityShenyang110036P.R.China Chongqing Key Laboratory of Natural Product Synthesis and Drug Research Chongqing 401331P.R.China

Presented herein is a facile and straightforward synthetic method for the construction of amides via Ni/NHC-catalyzed amidation of alcohols with amines. The strategy exhibits various advantages over existingmethods, including base metal catalysis, commercially available catalyst, removal of oxidant, good yields(up to 95%), good functional group tolerance and substrate generality. Moreover, the nature of the reaction was revealed by NMR spectroscopy and isolation of intermediates.

关键词： catalysis alcohols amines

Acetylation of alcohols and amines under visible light irradiation:diacetyl as an acylation reagent and photosensitizer

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Organic Chemistry Frontiers 2022年第2期9卷 311-319页

作者： Pengcheng Lian Ruyi Li Xiao Wan Zixin Xiang Hang Liu Zhiyu Cao Xiaobing Wan Key Laboratory of Organic Synthesis of Jiangsu Province College of ChemistryChemical Engineering and Materials ScienceSoochow UniversitySuzhou 215123China

This work developed an unprecedented strategy for the acetylation of alcohols and amines using diacetyl as both an acylation reagent and a photosensitizer.This environmentally friendly process exhibits excellent functional group tolerance,a wide substrate scope,operational simplicity and no need for the use of exogenous dehydrating reagents,activating reagents or photocatalysts.The potential application of this strategy to pharmaceutical chemistry was demonstrated by the late-stage modification of various drug molecules,and the process was found to be readily scalable without any loss of efficiency.Preliminary mechanistic results showed that the in situ generation of peracetic acid is responsible for the facile acylation of structurally diverse alcohols and amines using this technique.

关键词： technique. alcohols amines

Rhodium-catalyzed coupling-cyclization reaction of isocyanides and 2-azidophenyloxyacrylates:synthesis of N-(3-substituted benzo[d]oxazol-2(3H)-ylidene)amines and dihydrobenzo[d]oxazoles

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Organic Chemistry Frontiers 2022年第2期9卷 407-412页

作者： Ming Yang Xue-Cen Xu Yue Gong Yu-Long Zhao Jilin Province Key Laboratory of Organic Functional Molecular Design&Synthesis Department of ChemistryNortheast Normal UniversityChangchun 130024China

A rhodium-catalyzed coupling cyclization of isocyanides with 2-azidophenyloxyacrylates has been developed for the first time.This reaction allows divergent syntheses of two significant N-heterocycles,fivemembered N-(3-substituted benzo[d]oxazol-2(3H)-ylidene)amines and dihydrobenzo[d]oxazoles,from readily available starting materials in a single step.

关键词： substituted catalyzed amines

Bond energy enabled amine distinguishing strategy:chemo-,regioselective 1,3-diamination of(trifluoromethyl)alkenes with different amines by two C(sp^(3))-F bond cleavages

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Organic Chemistry Frontiers 2022年第5期9卷 1383-1388页

作者： Hao Zeng Hengyuan Li Chengxi Li Huanfeng Jiang Chuanle Zhu School of Chemistry and Chemical Engineering Key Laboratory of Functional Molecular Engineering of Guangdong ProvinceSouth China University of TechnologyGuangzhou 510640China

The methods to distinguish between amines are rarely investigated.In this article,a bond energy enabled amine distinguishing strategy is reported.With(trifluoromethyl)alkenes as linchpins,a chemo-,regio-selective thre... 详细信息

关键词： amines alkenes energy

Trace amine-associated receptors at the cross-road between innate olfaction of amines, emotions, and adult neurogenesis

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Neural Regeneration Research 2022年第6期17卷 1257-1258页

作者： Evgeniya V.Efimova Nataliia V.Katolikova Evgeny V.Kanov Raul R.Gainetdinov Institute of Translational Biomedicine and Saint Petersburg University Hospital Saint Petersburg State UniversitySaint PetersburgRussia

Trace amines are the class of endogenous biogenic amines that traditionally include beta-phenylethylamine,p-tyramine,tryptamine,octopamine,and o thers.Many t race amines represent products of amino acids decarboxylation by bacterial decarboxylases during tissue putrefaction or by endogenous decarboxylases in the body.Production of trace amines by gut microbiota is also known(Berry et al.,2017;Gainetdinov et al.,2018).Thus,trace amines are enriched during the decomposition of proteins and concentrated in certain bodily fluids.

关键词： amines Berry concentrated

Photocatalytic divergent decarboxylative amination: a metal-free access to aliphatic amines and hydrazines

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Science China Chemistry 2021年第10期64卷 1756-1762页

作者： Xianli Shu Ruting Xu Saihu Liao Key Laboratory of Molecule Synthesis and Function Discovery(Fujian Province University) State Key Laboratory of Photocatalysis on Energy and EnvironmentCollege of ChemistryFuzhou UniversityFuzhou 350108China Beijing National Laboratory for Molecular Sciences Beijing 100190China

Nitrogen-containing motifs are widely present in natural products, bioactive molecules, and drugs. Accordingly, effective synthetic methods with high efficiency and diversity are highly desirable. Here, we present the invention of a facile, visible lightmediated decarboxylative C(sp^(3))–N bond-forming reaction by employing abundant carboxylic acids as the feedstock and a commercial diazirine as a nitrogen donor. This process is amenable to access both imines and diaziridines, as the corresponding masked amines and hydrazines, through a selectable single or double nitrogen transfer from the diazirine, respectively. This divergent approach works well in both directions with various alkyl carboxylic acids, including primary, secondary, and tertiary acids, as well as natural products and drugs, thus affording a rapid, metal-free approach to build nitrogen-containing molecule libraries with considerable structural diversity, which could thus benefit the related study in context of chemical biology and drug discovery.

关键词： decarboxylative amination divergent synthesis nitrogen transfer amines diazirines

Zinc Powder Catalysed Formylation and Urealation of amines Using CO2 as a C1 Building Block

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Chinese Journal of Chemistry 2020年第10期38卷 1057-1064页

作者： Chongyang Du Yaofeng Chen State Key Laboratory of Organometllic Chemistry Shanghai Institute of Organic ChemistryUniversity of chinese Academy of SciencesChinese Academy of Sciences345 Lingling RoadShanghai 200032China

Summary of main observation and conclusion Transformation of CO2 into valuable organic compounds catalysed by cheap and biocompatible metal I catalysts is one of important topics of current organic synthesis and catalysis.Herein,we report the zinc powder catalysed formylation and urealation of amines with CO2 and(EtO)zSiH under solvent free condition.Using 2 mol%zinc powder as the catalyst,a series of secondary amines,both the aromatic ones and the aliphatic ones,can be formylated into formamides.When primary aromatic amines were used as the substrates,the reactions produce urea derivatives.The electronic and steric effects from the substrates on the formylation and urealation reactions were observed and discussed.The recovery and reusability of zinc powder were investigated,showing the zinc powder can be reused in the formylation reaction without loss of catalytic activity.The analysis on the reactants/products mixture after filtering out the zinc powder showed the zinc concentration in the mixture is low to 1 ppm.The path-ways for the formylation and urealation of amines with this catalytic system were also investigated,and related to the different substrates.

关键词： amines aromatic mixture

Fe_(2)Mn(μ_(3)-O)(COO)_(6) Cluster Based Stable MOF for Oxidative Coupling of amines via Heterometallic Synergy

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Chinese Journal of Chemistry 2021年第11期39卷 2983-2989页

作者： Ying-Xia Wang Hui-Min Wang Pan Meng Dong-Xia Song Zhikai Qi Xian-Ming Zhang Key Laboratory of Magnetic Molecules and Magnetic Information Materials(Ministry of Education) Institute of Chemistry and CultureSchool of Chemistry and Material ScienceShanxi Normal UniversityLinfenShanxi041004 China College of Chemistry&Chemical Engineering Key Laboratory of Interface Science and Engineering in Advanced MaterialMinistry of EducationTaiyuan University of TechnologyNo.79 Yingze WestTaiyuanShanxi030024 China

The direct catalytic oxidative coupling of amines is one of the attracting methods for the synthesis of a variety of pharmaceutical or industrial needed imines.Numerous earth-abundant manganese based salts,oxides,and complexes have been applied in this reaction.However,these compounds suffered from difficult separation,large catalyst loading,complicated reactivation or indeterminate activity.Considering the facts that metal-organic frameworks(MOFs)with crystalline structure,precise composition,and enormous surface area have superior performance in heterogeneous catalytic reactions,herein,we introduced Mn into[Fe_(3)(μ_(3)-O)(CH_(3)COO)_(6)],one of the precursors for the preparation of stable MOFs,and got[Fe_(2)Mn(μ_(3)-O)(CH_(3)COO)_(6)]cluster.After ligand replacement with biphenyl-3,4’,5-tricarboxylic acid(BPTC),heterometallic cluster-based[Fe_(2)Mn(μ_(3)-O)(BPTC)2(DMF)2(H_(2)O)](1)was obtained.As expected,1 is stable and able to catalyze the homo-or cross-coupling of amines effectively and selectively with 0.9 mol%catalyst loading at room temperature.Control experiments indicated that the catalytic activity of 1 mainly stems from Mn sites and that Fe synergistically contributes to the stability.Additionally,1 is recyclable and can be reused easily for at least 8 runs without obvious decrease in catalytic ability.To our knowledge,1 should be the first heterometallic cluster-based MOF with defined structure suitable for the synthesis of diverse imines from oxidative coupling of amines under mild conditions,which may shed light on the easy preparation of effective heterogeneous catalysts for organic synthesis.

关键词： amines Metal-organic frameworks Manganese Oxidative coupling Heterometallic synergy