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palladium-catalyzed S_(N)2 glycosylation of phenols

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Science China Chemistry 2024年第4期67卷 1037-1038页

作者： Yu Zhu P.Andrew Evans Department of Chemistry Queen’s University90 Bader LaneKingstonK7L 3N6Canada Xiangya School of Pharmaceutical Sciences Central South UniversityChangsha 410013China

Glycosides are essential structural motifs present in an array of important medicines,materials,and natural products[1].Nevertheless,the chemo-and stereoselective construction of the glycosidic linkage is a long-standing challenge because relatively minor variations in the glycosyl donor or acceptor’s structure can impact stereoselectivity,thus influencing the product's functional properties.

关键词： properties palladium catalyzed

Enantioselective Synthesis of Benzimidazole Atropisomers Featuring a N-N Axis

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Chinese Journal of Chemistry 2024年第7期42卷 711-718页

作者： Fang-Bei Ge Qi-Kun Yin Chuan-Jun Lu Xuan Xuan Jia Feng Ren-Rong Liu College of Chemistry and Chemical Engineering Qingdao UniversityQingdaoShandong 266071China School of Pharmacy Key Laboratory of Mlecular Pharmacoogy and Drug EvaluationMinistry of EducationYantai Universit YantaiShandong 264005China

Atroposelective synthesis of N-N atropisomers is an emerging area but remains underexplored;in particular,the synthesis of N-N benzimidazole atropisomers is still unprecedented.Herein,the first enantioselective synthesis of N-N benzimidazole atropisomers via the palladium-catalyzed de novo construction of benzimidazole skeleton is presented.With readily available palladium catalyst and biphosphine ligand,a broad range of nonbiaryl benzimidazole and indole-benzimidazole atropisomers were conveniently ac-cessed in high yields and with excellent enantioselectivities.Significantly,these N-N benzimidazole atropisomers showed great anti-tumor activity and selectivity to breast cancer MCF-7 cells.The simple catalytic system,broad substrate scope,high enantioselectivi-ty,and good bioactivity make this approach highly attractive.

关键词： Asymmetric synthesis Atropisomerism palladium Benzimidazole Antitumor

S-,P-stabilized bromoallenes for modular allenylborylation of alkenes

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Science China Chemistry 2024年第1期67卷 360-367页

作者： Jixin Wang Donghao Luo Ying Hu Zhili Duan Jianlin Yao Konstantin Karaghiosoff Jie Li Key Laboratory of Organic Synthesis of Jiangsu Province Suzhou Key Laboratory of Pathogen Bioscience and Anti-infective MedicineCollege of ChemistryChemical Engineering and Materials ScienceSoochow UniversitySuzhou 215123China Department Chemie Ludwig-Maximilians-Universitat MunchenButenandtstr.5-13Haus F81377 MunichGermany State Key Laboratory and Institute of Elemento-Organic Chemistry Haihe Laboratory of Sustainable Chemical TransformationsCollege of ChemistryNankai UniversityTianjin 300071China

Simultaneously forming a carbon-carbon and a carbon-heteroatom bond in a single step through transition metal-catalyzed alkene difunctionalization strategy has emerged as a powerful tool for synthetic organic chemistry.Due to the uncontrollable reactivity,direct cross-coupling with bromoallenes as the building blocks for the selective allenation and borylation remains challenging.We herein report a new type of S-and P-stabilized bromoallenes for palladium-catalyzed modular allenation and borylation of alkenes to the divergent synthesis of multiply functionalized allenes in a highly regio-and diastereoselective manifold.The reaction features broad substrate scope and wide functional group compatibility,thus providing a straightforward method to install allenyl and boryl groups across alkenes.Control experiments highlight the crucial importance of S-,P-stabilization for the oxidative insertion of Pd-species into the allenyl-Br bond.The facile syntheses of bioactive allenic steroids and exocyclic allenes demonstrate the synthetic utility of this protocol.

关键词： alkene difunctionalization olefins bromoallenes allenylborylation palladium

Recent Advances in Catalytic Carbonylation Reactions in Alternative Reaction Media

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Chinese Journal of Chemistry 2024年第4期42卷 406-429页

作者： Csaba Árvai László T.Mika Department of Chemical and Environmental Process Engineering Faculty of Chemical Technology and BiotechnologyBudapest University of Technology and EconomicsMűegyetem rkp.3H-1111 BudapestHungary

Since the discovery of the hydroformylation(oxo-synthesis or Roelen reaction)and the Reppe-reaction,the transition metal-catalyzed carbonylation reactions,providing versatile,facile,and even atom-economic methods for the selective incorporation of C=O functionality to various skeletons,have gained tremendous importance in synthetic organic chemistry from laboratories to industrial applications.The carbonylation of carbon-carbon multiple bonds,aromatic halides,triflates,etc.,in the presence of various nucleophiles has led the way to produce aldehydes,carboxylic acids,esters,amides,etc.,in the fine chemical industry.However,these protocols usually proceed in conventional,fossil-based,and usually toxic reaction environments.Thus,several attempts have been directed to developing efficient carbonylation methods in alternative,less harmful,non-fossil-based and even in renewable reaction media.In this review,we overview the recent applications of alternative solvents such as water,biomass-based alcohols,γ-valerolactone(GVL),2-methyltetrahydrofuran(2-MeTHF),ionic liquids(ILs),deep eutectic solvents(DES),alkyl levulinates,limonene,α-pinene,and dimethyl carbonate as well as fluorous media to improve efficiency,safety and environmentally benign nature of carbonylation protocols.

关键词： Carbonylation Catalysis Solvents Green chemistry Carbon monoxide Transition metals Homogeneous catalysis palladium

S1-supported Pd@CeO_(2) quasi-core@shell materials as advanced catalysts for selective hydrogenation of furfural

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Chinese Chemical Letters 2024年第3期35卷 493-496页

作者： Xiang Chu Lingling Zhang Ke Wang Rui Zhang Xiao Wang Shuyan Song Hongjie Zhang State Key Laboratory of Rare Earth Resource Utilization Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchun 130022China School of Applied Chemistry and Engineering University of Science and Technology of ChinaHefei 230026China

Bare Pd metal nanoparticles invariably suffer from poor selectivity in furfural hydrogenation by forming flat configurations,with the aromatic ring of the substrate molecules parallel to the metal surface.Herein,we put forward a promising solution by using CeO_(2)as promoters to modify Pd nanoparticles for modulating the adsorption behaviors of furfural molecules.To achieve the highly-desired ultra-small Pd@CeO_(2)core@shell nanostructure,a“constrained auto-redox”synthesis is developed,in which silicalite-1 supports play the key role of providing their surface as the landing place of PdO_(x)precursors for inhibiting the overgrowth and the deformation.To the best of our knowledge,this is one of the smallest core@shell materials obtained from aqueous synthesis.When evaluated as catalysts,Pd@CeO_(2)/S-1 gives 98.9%conversion of furfural with 94.3%selectivity for furfural alcohol in 15 h,which is much better than that of Pd/S-1(88.6%conversion with 44.3%selectively).The DFT simulation reveals a strong interaction between the defects of CeO_(2)and the oxygen atom of the–CHO group in furfural molecules,which benefits the selective hydrogenation occurred in the–CHO group rather than the furan ring.

关键词： Core@shell palladium Ceria Auto-redox synthesis Hydrogenation

palladium-catalyzed tandem Heck/carbonylation/ aminocarbonylation en route to chiral heterocyclic α-ketoamides

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Organic Chemistry Frontiers 2022年第4期9卷 939-945页

作者： Huaanzi Hu Ting Yu Sidi Cheng Jing Li Chunfang Gan Shuang Luo Qiang Zhu State Key Laboratory of Respiratory Disease Guangzhou Institutes of Biomedicine and HealthChinese Academy of Sciences190 Kaiyuan AvenueGuangzhou 510530China School of Pharmacy Changzhou UniversityChangzhouJiangsu 213164China University of Chinese Academy of Sciences No.19(A)Yuquan RoadShijingshan DistrictBeijing100049China Guangxi Key Laboratory of Natural Polymer Chemistry and Physics College of Chemistry and MaterialsNanning Normal UniversityNanning 530001China Bioland Laboratory(Guangzhou Regenerative Medicine and Health Guangdong Laboratory) 510005 GuangzhouChina

An unprecedented tandem carbonylation/aminocarbonylation triggered by palladium-catalyzed enantio-selective Heck-type exocyclopalladation delivering chiral heterocyclicα-ketoamides has been developed.The uncommon double CO insertion into theσ-alkylpalladium intermediate takes place selectively under atmospheric pressure of CO using alkylamine as the nucleophile.Unique structures hybridizing alkylα-ketoamides with indolin-2-one containing a C3 all-carbon quaternary stereogenic center and 5,7-dihydro-6H-dibenzo[b,d]azepin-6-one containing a thermodynamically stabilized stereogenic biaryl axis are produced in good yields with excellent enantio-and/or diastereoselectivities.

关键词： heterocyclic palladium catalyzed

palladium-Catalyzed Intramolecular Dehydrogenative Arylboration of Alkenes

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Chinese Journal of Chemistry 2022年第20期40卷 2437-2444页

作者： Chenchen Zou Hongli Wu Yuqi Ji Penglin Zhang Huanhuan Cui Genping Huang Chun Zhang Institute of Molecular Plus Tianjin Key Laboratory of Molecular Optoelectronic ScienceDepartment of ChemistrySchool of ScienceTianjin UniversityTianjin300072 China State Key Laboratory of Elemento-Organic Chemistry Nankai UniversityTianjin300071 China

The palladium-catalyzed borylative cyclization via C—H activation has been developed.By this chemistry,the indole-fused dihydro-pyrrole motif,which is a kind of important unit in natural products and bio-active molecules,could be constructed and installed with a boric ester group.Furthermore,the utilities of products have been illustrated by the study of further transformations.Importantly,by using chiral ligand,the enantioselectivity of this borylative cyclization reaction could be controlled.Moreover,the borylative mechanism,which should proceed through a Pd(II)/Pd(IV)catalytic cycle,has been proposed based on the DFT calculations.

关键词： palladium Dehydrogenative coupling reaction Indole-fused dihydro-pyrrole Boron

palladium Iodide-Catalyzed Selective Carbonylative Double Cyclization of 4-(2-Aminophenyl)-3-yn-1-ols to Dihydrofuroquinolinone Derivatives

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Chinese Journal of Chemistry 2023年第21期41卷 2801-2809页

作者： Raffaella Mancuso Alex De Salvo Patrizio Russo Aurelia Falcicchio Nicola Della Ca’ Leonardo Pantoja Munoz Bartolo Gabriele Laboratory of Industrial and Synthetic Organic Chemistry(LISOC) Department of Chemistry and Chemical TechnologiesUniversity of CalabriaVia Pietro Bucci 12/C87036 Acavacata di Rende(CS)Italy Institute of Crystallography National Research CouncilVia Amendola122/O70126 BariItaly Department of Chemistry Life Sciences and Environmental Sustainability(SCVSA)University of ParmaParco Area delle Scienze17/A43124 ParmaItaly Department of Natural Sciences Faculty of Science and TechnologyMiddlesex UniversityThe BurroughsNW44BT LondonUK

The PdI_(2)/KI-catalyzed oxidative carbonylation of 4-(2-aminophenyl)-3-yn-1-ols,bearing two potential nucleophilic groups in suitable position selectively leads to dihydrofuroquinolinone derivatives in fair to high yields(60%—89%)and excellent turnover numbers(180—267 mol of product per mol of Pd)over 19 examples,through a mechanistic pathway involving initial O-cyclization followed by N-cyclocarbonylation.In such process,the selective catalytic construction of two rings and three new bonds is achieved in one synthetic step to afford high value added fused heterocyclic structures starting from readily available materials.

关键词： Carbonylation Cyclization Heterocycles palladium Polycyclic heterocycles

palladium-Catalyzed Oxidative Alkynylation of Allenyl Ketones: Access to 3-Alkynyl Poly-substituted Furans

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Chinese Journal of Chemistry 2023年第24期41卷 3598-3604页

作者： Bowen Dou Kang Wang Jianbo Wang Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education College of ChemistryPeking UniversityBeijing100871 China The State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of Sciences354 Fenglin LuShanghai200032 China

Furans bearing alkynyl substituents are highly useful in organic synthesis.However,the methodologies to access these important furan derivatives are rather limited.We herein report an efficient synthesis of alkynylated furan derivatives based on Pd-catalyzed oxidative cross-coupling reaction between allenyl ketones and terminal alkynes.This novel synthesis of alkynylated furans with wide substrate scope is operationally simple and tolerates various functional groups.Mechanistically,the formation of the palladium carbene through cycloisomerization and the subsequent alkynyl migratory insertion are proposed as the key steps in the transformation.The reaction reported in this paper further demonstrates the generality of the carbene-based cross coupling.

关键词： Allenyl ketones Oxidative alkynylation Cyclization Isomerization Furans Catalysis palladium Cross-coupling