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Recent Advances in Pd-Catalyzed Reactions Involving the “On-Water” Mechanism

Chinese Journal of Chemistry 2024年第5期42卷 533-542页

作者： Dong Wei guo-qiang lin State Key Laboratory of Systems Medicine for Cancer Shanghai Cancer InstituteShanghai Key Laboratory of Systems Regulation and Clinical Translation for CancerRen Ji HospitalShanghai Jiao Tong University School of MedicineShanghai200127 China State Key Laboratory of Chemical Biology Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai200032 China

As the chemical industry grapples with the need for more eco-friendly practices,the use of water as a reaction medium is gaining attraction in organic *** mini-review delves into Pd-catalyzed reactions that utilize the "on-water" mechanism,spanning from 2019 to late *** reactions are neatly categorized into several types: (A) Catalytic C—H activations,(B) Mizoroki- Heck-type reactions,(C) Suzuki-Miyaura reactions,and (D) Cyclization *** showcasing the potential of water as a sustainable reaction medium for organic transformations,these reactions leave no doubt about the importance of embracing eco-friendly practices in the chemical *** Scientists In 1980,a seminal work by Breslow et *** an acceleration of reaction rate in the Diels-Alder *** and co-workers noted a significant increase in the rate of the [2σ+2σ+2π] cycloaddition of quadricyclane and dimethyl azodicarboxylate (DMAD) when the reaction was conducted in water,as opposed to when it was carried out in organic *** term "on-water" was then coined to describe this *** strategy was further expanded to transition-metal catalyzed transformations by Ackermann in ***,Varma and Leazer disclosed a Pd-catalyzed Mizoroki-Heck type arylation of alkenes with diaryliodonium salts “on-water”.The enantioselective version of "on-water" process was not realized until 2014 by the Zhou *** on,the Schaub group described a Pd-catalyzed Suzuki–Miyaura coupling reaction of electron-poor aryl chlorides with water,using only 50 ppm of catalyst *** recently,Liu and lin extended the "on-water" strategy to Pd-catalyzed double Mizoroki-Heck *** mini-review has focused on Pd-catalyzed reactions involving the “on-water” mechanism.

关键词： Pd-catalyzed “On-water” Green chemistry Aqueous reactions Mechanism Methodology and reactions Mizoroki-Heck reaction Cross-coupling

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Functionalization of C,C-palladacycles:application in the synthesis of functional molecules

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Science China Chemistry 2023年第10期66卷 2721-2733页

作者： Dong Wei guo-qiang lin State Key Laboratory of Systems Medicine for Cancer Shanghai Cancer InstituteRen Ji HospitalShanghai Jiao Tong University School of MedicineShanghai 200127China Key Laboratory of Synthetic Chemistry of Natural Substances Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

Significant advancements have been achieved in the field of C,C-palladacycles functionalization in recent decades,which have greatly contributed to the synthesis of intricate drug molecules,natural products,innovative materials,and chiral ***,these advancements have led to the establishment of highly efficient and atom-economic synthetic *** on the differences in the C–Pd bonds,C,C-palladacycles can be further classified into several main types:C(aryl),C(alkyl)-,C(aryl),C(aryl)-,C(aryl),C(vinyl)-,and C(alkyl),C(carbonyl)-*** minireview will highlight the recent advances in the synthesis of functional molecules through the functionalization of different C,C-palladacycles,and we hope this survey will inspire future strategic developments for C,C-palladacycle catalysts and their synthetic application.

关键词： C,C-palladacycles functionalization synthetic application

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Carbon-hydrogen activation in China

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Science China Chemistry 2015年第8期58卷 1245-1248页

作者： Zhang-Jie Shi guo-qiang lin College of Chemistry and Molecular Engineering Peking University Shanghai Institute of Organic Chemistry Chinese Academy of Sciences

Transition metal catalyzed C-H Functionalization is one of the most important and challenging research fields in or- ganic chemistry and has rapidly evolved in recent decades. Some recent achievements in the field include i） minimizing the pre-activation procedures of substrates, ii） reducing waste production, and iii） shortening synthetic steps by de- veloping direct activations and straightforward transfor- mations of C-H bonds. With the rapid developments in chemistry and the continuous support of the Chinese gov- ernment, Chinese chemists have played important roles in this emerging field in the past two decades. To stimulate the continued success of Chinese chemists, this work provides an intensive account of the current status of this important field in China's Mainland.

关键词： Activation analysis Transition metals

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Synthesis of Substituted Naphthalenes by 1,4-Palladium Migration Involved Annulatlon w,th Internal Alkynes

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Chinese Journal of Chemistry 2018年第8期36卷 743-748页

作者： Dong Wei Tian-Jiao Hu Chen-guo Feng guo-qiang lin School of Physical Science and Technology ShanghaiTech University Shanghai 200031 China Key Laboratory of Synthetic Chemistry of Natural Substances Center for Excellence in Molecular Synthesis Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences Shanghai 200032 China Innovation Research Institute of Traditional Chinese Medicine Shanghai Uni- versity of Traditional Chinese Medicine Shanghai 201203 China

The palladium catalyzed annulation of 1-bromo-2-vinylbenzene derivatives with internal alkynes was realized for the efficient synthesis of substituted naphthalenes. A controllable aryl to vinylic 1,4-palladium migrati... 详细信息

关键词： metal migration naphthalene palladium annulation alkyne

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Performance of an electron linear accelerator for the first photoneutron source in China

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Nuclear Science and Techniques 2019年第4期30卷 1-7页

作者： Xuan Li Jun-qiang Zhang guo-qiang lin Wen-Cheng Fang qiang Gu Meng Zhang Shanghai Institute of Applied Physics Chinese Academy of Sciences Shanghai Synchrotron Radiation Facility Chinese Academy of Sciences University of Chinese Academy of Sciences

A compact 15.0-MeV, 1.5-kW electron linear accelerator(linAC) was successfully constructed to provide an electron beam for the first photoneutron source at the Shanghai Institute of Applied Physics, Shanghai,China. This linAC consists of five main parts: a thermal cathode grid-controlled electron gun, a pre-buncher, a variable-phase-velocity buncher, a light-speed accelerating structure, and a high-power transportation beamline. A digital feedforward radio frequency compensator is adopted to reduce the energy spread caused by the transient beam loading effect. Furthermore, a real-time electron gun emission feedback algorithm is used to keep the beam stable. After months of efforts, all the beam parameters successfully met the requirements of the facility. In this paper, the beam commissioning process and performance of the linAC are presented.

关键词： Electron linear accelerator High-power transportation beamline Digital feedforward radio frequency compensation Real-time electron gun emission feedback algorithm Transmission efficiency

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Influence of Nitrogen Vacancy Concentration on Mechanical and Electrical Properties of Rocksalt Zirconium Nitride Films

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Acta Metallurgica Sinica(English Letters) 2017年第11期30卷 1100-1108页

作者： Ke-Chang Han guo-qiang lin Chuang Dong Kai-Ping Tai Xin Jiang Key Laboratory for Material Modification by Laser Ion and Electron Beams(Ministry of Education)Dalian University of Technology Institute of Metal Research Chinese Academy of Sciences

To study the influence of the nitrogen vacancy （VN） on mechanical and electrical properties of zirconium nitride deeply, ZrNx films with different VN concentrations were synthesized on the Si （111） substrates by enhanced magnetic filtering arc ion plating. The morphologies, microstructures, residual stresses, compositions, chemical states, mechanical and electrical properties of the as-deposited films were characterized by field-emission scanning electron microscopy, X-ray diffraction, X-ray photoelectron spectrometry, Nanoindenter and Hall effect measurements. The results showed that ZrNx films exhibited rocksalt single-phase structure within a VN concentration ranging from 26 to 5%. The preferred orientation, thickness, grain size and residual stress of the ZrNx films kept constant at different VN concentrations. Both the nanohardness and elastic modulus first increased and then decreased with the decrease in VN concentration, reaching the peaks around 16%. And the electric conductivity of the ZrNx films showed a similar tendency with nanohardness. The underlying atomic-scale mechanisms of VN concentration-dependent hardness and electric conductivity enhancements were discussed and attributed to the different electronic band structures, rather than conventional meso-scale factors, such as preferred orientation, grain size and residual stress.

关键词： ZrN_x films Nitrogen vacancy Hardness Electrical properties Band structure

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Effect of Axial Magnetic Field on the Microstructure and Mechanical Properties of CrN Films Deposited by Arc Ion Plating

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Acta Metallurgica Sinica(English Letters) 2016年第6期29卷 546-553页

作者： Yan-Hui Zhao Li Xu Chao-Qian guo Wen-Jin Yang guo-qiang lin Bao-Hai Yu Institute of Metal Research Chinese Academy of Sciences Key Laboratory of Materials Modification by Laser Ion and Electron Beams (Dalian University of Technology) Ministry of Education Dalian University of Technology

CrN films were deposited on the high-speed-steel substrates by arc ion plating. The effect of an axial magnetic field on the microstructure and mechanical properties was investigated. The chemical composition, microstructure, surface morphology, surface roughness, hardness and film/substrate adhesion of the film were characterized by X-ray photoelectron spectroscopy, X-ray diffraction, scanning electron microscope（SEM）, surface morphology analyzer, Vickers microhardness test and scratch test. The results showed that the magnetic field puts much effect on the microstructure,chemical composition, hardness and film/substrate adhesion of the Cr N films. The N content increases and Cr content decreases when the magnetic flux density increases from 0 to 30 m T. All of the Cr N films were found to be substoichiometric. With an increase in the magnetic flux density, the film structures change in such way： Cr_2N →Cr_（2-N）＋CrN→CrN＋Cr_2N→*** SEM results showed that the number of macroparticles（MPs） on the film surface is significantly reduced when the magnetic flux density increases to 10 mT or higher. The surface roughness decreases with the magnetic field, which is attributed to the fewer MPs and sputtered craters on the film surface. The hardness value increases from 2074 HV_（0.025） at 0 mT（without magnetic field） and reaches a maximum value of 2509 HV_（0.025） at 10 m *** further increase in the magnetic flux density leads to a decrease in the film hardness. The critical load of film/substrate adhesion shows a monotonous increase with the increase in magnetic flux density.

关键词： Magnetic field Arc ion plating CrN films Hardness Adhesion

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A New Synthesis of 4, 4-Diaryl/Diheteroaryl-3-butenyl Derivatives of Nipecotic Acids as GABA Transporter Inhibitors

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Chinese Chemical Letters 2005年第9期16卷 1205-1208页

作者： Jian Ge ZHANG Chang Sheng JIANG guo qiang lin Ren WEN Department of Medicinal Chemistry School of Pharmacy Fudan University Shanghai 200032 Shanghai Institute of Organic Chemistry Chinese Academy of Sciences shanghai 200032

A new method for the synthesis of 4, 4-diaryl/diheteroaryl-3-butenyl derivatives of nipecotic acid as GABA transporter inhibitors is described. The key intermediates 4-tosyl-1, 1-diaryl/diheteroaryl-1-butene 10a-d were synthesized by Wittig reaction, and followed by alkylation with （R）-3-piperidinecarboxylate. The resulting N-cycloalkylated amino acid esters 11a-d were saponified and then acidified to get the target compounds 1a-d. The preliminary bioassays showed that la-d exhibited excellent inhibition of [3H]-GABA uptake in vitro of culture cells.

关键词： Tiagabine nipecotic acid derivatives synthesis GABA transporter inhibitor

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Trisubstituted alkenes featuring aryl groups:stereoselective synthetic strategies and applications

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Science China Chemistry 2023年第5期66卷 1261-1287页

作者： Meng-Yao Li Shuyang Zhai Xiao-Mei Nong Ao Gu Jiatong Li guo-qiang lin Yingbin Liu Shanghai Cancer Institute Renji Hospital Affiliated to Shanghai Jiao Tong University School of MedicineShanghai 200127China Shanghai Institute of Organic Chemistry Chinese Academy of SciencesShanghai 200032China School of Basic Medicine and Clinical Pharmacy China Pharmaceutical UniversityNanjing 211198China

In recent years,the synthesis and application of alkenes have attracted increased ***(TriPEs)have lower molecular torsion than tetraphenylethenes(TPEs),which helps to balance the degree of conjugation and the aggregation-induced emission(AIE)*** geometry of double bonds has a significant impact on ***,it is essential to provide a comprehensive summary of the stereoselective synthetic strategies for trisubstituted *** this review,common strategies for the stereoselective synthesis of alkenes are described,with an emphasis on the origin of stereoselectivity and the types of *** addition,the AIE properties of TriPE and its applications in optoelectronic devices,stimuli-responsive materials,sensors,and therapies were discussed.

关键词： trisubstituted alkenes stereoselective synthesis aggregation-induced emission transition metal catalysis

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Stereoselective Access to Polypropionates Expedited by the Double Hydroboration of Allenes: Total Synthesis of Antitumor (−)-Pironetin

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CCS Chemistry 2021年第2期3卷 769-779页

作者： lin Yang Luyao Kong Qi Gu Shunjie Shao guo-qiang lin Ran Hong CAS Key Laboratory of Synthetic Chemistry of Natural Substances Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032 University of Chinese Academy of Sciences Beijing 100049

Polyketides,a large class of secondary metabolites,have been of long-standing interest to the synthetic community due to their intriguing biological activities and structural versatility and complexity.A typical structural unit of various natural products,polypropionate,has prompted enormous efforts in the development of novel synthetic methods and strategies in the past five *** this study,a non-aldol-type approach based on double hydroboration of allenes has been developed to provide a powerful method for the stereodivergent construction of various polyol stereotriads and stereotetrads that are amenable for synthesizing *** stereochemical control is possibly attributable to the boronate complex that aligned itself as a rigid conformation for the second stereoselective hydroboration reaction by suppressing the barotropic rearrangement of allylborane *** feasibility of preparing the key polypropionate motif facilitates the efficient synthesis of(-)-pironetin,a potentα-tubulin inhibitor halting the cell cycle at M phase.

关键词： allene boronate complex hydroboration,polypropionate total synthesis

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