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Stereochemical editing:Catalytic racemization of secondary alcohols and amines

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Chinese Chemical Letters 2024年第5期35卷 17-31页

作者： Jun Zhang Zhiyao Zheng Can Zhu department of chemistry Fudan UniversityShanghai 200438China department of organic chemistry Arrhenius LaboratoryStockholm UniversityStockholm 10691Sweden

Chiral alcohols and amines are important structural units widely existing in pharmaceuticals,agrochemicals,and food *** kinetic resolution(DKR)is an efficient strategy to deliver optically active alcohols and amines from their *** the development of DKR method,racemization catalyst plays as a crucial element with the requirement of compatibility with the kinetic resolution(KR)*** this paper,recent advance in the catalytic racemization of secondary alcohols and amines is summarized based on different types of racemizing intermediates,which are redox racemization via ketone/imine intermediates,racemization via radical intermediates,and racemization via carbocation *** racemization of secondary alcohols and amines is also enclosed.

关键词： Racemization Secondary alcohols Amines Kinetic resolution Dynamic kinetic resolution

Cobalt(Ⅲ)hydride HAT mediated enantioselective intramolecular hydroamination access to chiral pyrrolidines

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Science China chemistry 2024年第6期67卷 2002-2008页

作者： Qi Meng Tao Qin Huanran Miao Ge Zhang Qian Zhang Jilin Province Key Laboratory of organic Functional Molecular Design&Synthesis Department of ChemistryNortheast Normal UniversityChangchun130024China State Key Laboratory of Organometallic chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai200032China

Enantioenriched pyrrolidines and derivatives are ubiquitous substructures in compounds of importance to medicinal and biological ***,we report an efficient cobalt-catalyzed intramolecular asymmetric hydroamination reaction that produces chiral pyrrolidines with good to excellent yield and *** with previously reported radicalinvolved methodologies for enantioenriched pyrrolidines,these conditions feature two elegant versatilities,enabling(1)the use of cobalt-catalyzed hydrogen atom transfer(HAT)to generate organocobalt intermediates that bring radical reaction to organometallic chemistry,and(2)enantioselective intramolecular C-N bond forging through an S_(N)2-like displacement involving dynamic kinetic resolution(DKR).This approach provides a new alternative and efficient methodology for enantioselective radical-involved C-N bond construction that can be used in the synthesis of both chiral pyrrolidines and homologous nitrogen heterocycles.

关键词： asymmetric catalysis radical hydroamination cobalt catalysis hydrogen atom transfer

Synthesis of uniform two-dimensional MoS_(2) films via thermal evaporation

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Nano Research 2024年第4期17卷 3217-3223页

作者： Xue-Wei Lu Zhewei Li Chen-Kai Yang Weijia Mou Liying Jiao Key Laboratory of organic Optoelectronics and Molecular Engineering of the Ministry of Education Department of ChemistryTsinghua UniversityBeijing 100084China

Two-dimensional(2D)molybdenum disulfide(MoS_(2))holds great potential for various applications such as electronic devices,catalysis,lubrication,anti-corrosion and so *** evaporation is a versatile thin film deposition technique,however,the conventional thermal evaporation techniques face challenges in producing uniform thin films of MoS_(2) due to its high melting temperature of 1375℃.As a result,only thick and rough MoS_(2) films can be obtained using these *** address this issue,we have designed a vacuum thermal evaporation system specifically for large-scale preparation of MoS_(2) thin *** using K2MoS4 as the precursor,we achieved reliable deposition of uniform polycrystalline MoS_(2) thin films with a size of 50 mm×50 mm and controllable thickness ranging from 0.8 to 2.4 *** approach also allows for patterned deposition of MoS_(2) using shadow masks and sequential deposition of MoS_(2) and tungsten disulfide(WS_(2)),similar to conventional thermal evaporation ***,we have demonstrated the potential applications of the obtained MoS_(2) thin films in field effect transistors(FETs),memristors and electrocatalysts for hydrogen evolution reaction(HER).

关键词： thermal evaporation molybdenum disulfide two-dimensional memristors hydrogen evolution reaction

Electric-field-controlled highly regioselective thiocyanation of N-containing heterocycles

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Science China chemistry 2024年第4期67卷 1263-1269页

作者： Ming Gong Qian Wu Jung Keun Kim Mengmeng Huang Yabo Li Yangjie Wu Jong Seung Kim Henan Key Laboratory of Chemical Biology and organic chemistry Key Laboratory of Applied Chemistry of Henan UniversitiesCollege of ChemistryZhengzhou UniversityZhengzhou 450052China department of chemistry Korea UniversitySeoul 02841Korea

Achieving highly regioselective synthesis in organic chemistry is challenging due to the uncontrollable orientation between reacting *** electric fields(EEFs)can influence the reactivity and selectivity of the substrate by causing directional ***,scalable and efficient techniques for using EEFs as“smart catalysts”have been lacking,hindering their *** this study,we present a novel method for modifying the regioselectivity of quinoxaline-2(1H)-ones by functionalizing their C7-position using the electric double layer(EDL)*** approach led to moderate to good yields of the corresponding C7-thiocyanation *** calculations and control experiments demonstrated that EEFs could reverse the regioselectivity of quinoxaline-2(1H)-ones,allowing the C7-thiocyanation to proceed via a radical reaction ***,the resulting 7-thiocyano-1-methylquinoxaline-2(1H)-ones exhibited promising AIE *** work showcases a promising strategy for achieving highly regioselective functionalization by aligning the electric field with the desired reaction/bond axis.

关键词： electric fields reaction-axis rule electric double layer C7-thiocyanation C-S bond formation

Regioselective C-C bond cleavage/aminocarbonylation cascade under copper catalysis

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Science China chemistry 2024年第11期67卷 3798-3806页

作者： Qi-Chao Shan Yan Zhao Yong Wu Hong-Fei Liu Xin-Hua Duan Li-Na Guo department of chemistry School of Chemistry Energy Research Center of Energy Storage Materials and Devices Ministry of EducationXi'an Jiaotong University State Key Laboratory of Applied organic chemistry Lanzhou University

A regioselective C-C bond cleavage/aminocarbonylation cascade is presented. In recent years, tremendous progress has been made in the alkoxyl radical-mediated C-C bond cleavage of unstrained monocarbocycles. In contrast, the deconstruction and functionalization of bicyclic skeletons has been less developed and has mainly focused on the ring expansion process. Inspired by the aromatization-driven C-C bond cleavage, here we demonstrate a ring-opening/aminocarbonylation cascade under copper catalysis, in which the formation of a stable γ-lactam or succinimide skeleton reverses the selectivity of C-C cleavage. Remarkably, the photo and thermal assistance is not required when the succinimide skeleton is formed during the ring opening process. DFT calculations revealed that this unexpected ring-opening process is thermodynamically and kinetically favourable.

关键词： C-C bond cleavage controllable regioselectivity aminocarbonylation bicyclic alkoxy radical

Recent advances in the synthesis and application of N-heterocyclic carbene-based molecular cages

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Science China chemistry 2024年第5期67卷 1510-1523页

作者： Qiongjie Chai Lixin Duan Yanzhe Ma Tianheng Hou Tao Tu Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials Department of ChemistryFudan UniversityShanghai 200438China State Key Laboratory of Organometallic chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

N-Heterocyclic carbene(NHC)-based cages have emerged as a prominent and dynamic research area within the research field of chemistry. Leveraging the distinctive electronic and steric properties of NHC ligands, the design, synthesis, and application of these corresponding cages have garnered substantial scholarly interest. In recent years, we have witnessed the successful fabrication of diverse NHC-based cages through a range of synthetic methodologies, which hold significant potential for applications in molecular recognition and catalysis. In this review, we delve into the foundational synthetic strategies that underlie the creation of NHC-based cages, employing approaches encompassing metal–NHC chelation, coordination assembly,and covalent bonding. Additionally, we compile the diverse applications of these cages within catalytic processes and molecular recognition. Lastly, we shed light on the current limitations of synthesis and outline future trends in the development of NHCbased cages.

关键词： N-heterocyclic carbene molecular cages supramolecular chemistry synthetic strategies applications

Copper-catalyzed conjugate addition of allene-derived nucleophiles to alkenyl-substituted carboxamides

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Chinese Chemical Letters 2024年第3期35卷 239-242页

作者： Bin Fu Yue Zhao Xiuping Yuan Yanfei Li Jianjun Yin Simin Wang Tao Xiong Qian Zhang Jilin Province Key Laboratory of organic Functional Molecular Design&Synthesis Department of ChemistryNortheast Normal UniversityChangchun 130024China State Key Laboratory of Organometallic chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China School of chemistry and Environmental Engineering Changchun University of Science and TechnologyChangchun 130012China

Catalytic Michael addition reaction represents a fundamental importance in organic synthetic *** corresponding conversions toward intrinsically low reactive enamide remains an ongoing *** herein report a copper-catalyzed conjugate addition of allenes toβ-substituted alkenyl amides,one of the most challenging Michael *** present method utilizes readily available allenes as the latent carbon-based nucleophiles and simple,commonβ-substituted alkenyl amides as starting materials,unlike previous methods that usually preinstall an activating group to improve the reactivity of amide or uses highly reactive stoichiometric quantities of ***,this approach shows good functional group compatibility and can be implemented under mild reaction conditions with excellent level of chemo-and regioselectivities.

关键词： CuH catalysis Allenes Unsaturated amide Conjugate addition Regioselectivity

Radical Arbuzov Reaction

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CCS chemistry 2024年第5期6卷 1312-1323页

作者： Linxiang Chai Jian Wang Jimin Yang Junyue Yin Zhuyong Zhang Yulu Cheng Lin Zhu Xiao-Song Xue Chaozhong Li department of chemistry University of Science and Technology of ChinaHefeiAnhui 230026 Shanghai Institute of organic chemistry Chinese Academy of SciencesShanghai 200032

The Arbuzov reaction(also known as the Michaelis–Arbuzov reaction)is one of the most fundamental transformations in organic chemistry and has been extensively used for the synthesis of organophosphorus compounds for over a ***,the reaction generally requires an elevated temperature and is applicable mainly to primary alkyl halides with poor functional group *** report herein a radical alternative to the conventional nucleophilic substitution ***,new radical phosphonylation reagents,9-fluorenyl o-phenylene phosphite and benzhydryl o-phenylene phosphite,have been developed for this *** photoredox-catalyzed reaction of a wide range of alkyl bromides or iodides with 9-fluorenyl(or benzhydryl)o-phenylene phosphite followed by workup with methanol(or ethanol)provides the corresponding dimethyl(or diethyl)alkylphosphonates in satisfactory yields at room temperature under mild *** method is applicable to primary,secondary,and even tertiary alkyl iodides and bromides and exhibits an excellent functional group tolerance,thereby enabling the late-stage modification of complex molecules and rapid synthesis of phosphonate-containing natural products and drug molecules.A mechanism involving the formation and subsequentβ-scission of phosphoranyl radicals is proposed.

关键词： Arbuzov reaction radicals phosphonylation photoredox catalysis alkyl halides

Supramolecular systems for bioapplications:recent research progress in China

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Science China chemistry 2024年第5期67卷 1397-1441页

作者： Yue-Yang Liu Xiao-Yong Yu Yu-Chen Pan Hang Yin Shuang Chao Yujie Li He Ma Minzan Zuo Kun-Xu Teng Jun-Li Hou Yong Chen Dong-Sheng Guo Ruibing Wang Yuxin Pei Zhichao Pei Jiang-Fei Xu Xiao-Yu Hu Chunju Li Qing-Zheng Yang Leyong Wang Yu Liu Zhan-Ting Li State Key Laboratory of Organometallic chemistry Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional MoleculesShanghai Institute of Organic ChemistryChinese Academy of SciencesUniversity of Chinese Academy of SciencesShanghai 200032China department of chemistry Fudan UniversityShanghai 200438China College of chemistry State Key Laboratory of Elemento-Organic ChemistryCollaborative Innovation Center of Chemical Science and EngineeringNankai UniversityTianjin 300071China State Key Laboratory of Quality Research in Chinese Medicine Institute of Chinese Medical SciencesUniversity of MacaoMacao 999078China College of chemistry&Pharmacy Northwest A&F UniversityYangling 712100China Key Lab of organic Optoelectronics&Molecular Engineering Department of ChemistryTsinghua UniversityBeijing 100084China College of Materials Science and Technology Nanjing University of Aeronautics and AstronauticsNanjing 211106China Key Laboratory of Radiopharmaceuticals Ministry of EducationCollege of ChemistryBeijing Normal UniversityBeijing 100875China Tianjin Key Laboratory of Structure and Performance for Functional Molecules College of ChemistryTianjin Normal UniversityTianjin 300387China State Key Laboratory of Analytical chemistry for Life Science Jiangsu Key Laboratory of Advanced Organic MaterialsSchool of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023China

Supramolecular systems feature dynamic,reversible and stimuli-responsive characteristics,which are not easily achieved by molecular *** last decade has witnessed tremendous advances in the investigations of supramolecular systems for various bioapplications,which include drug delivery,anticancer therapy,antibacterial therapy,photodynamic therapy,photothermal therapy,combination therapy,antidotes for residual drugs or toxins,and bioimaging and ***-guest chemistry has played a key role in the development of such bioactive supramolecular systems,and natural macrocycles(such as cyclodextrins),synthetic macrocycles(such as calixarenes,cucurbit[n]urils,and pillararenes),and porous framework polymers(such as supramolecular organic frameworks and flexible organic frameworks)have been most successfully used as hosts to build different kinds of host-guest systems for attaining designed *** self-assembly of rationally designed amphiphilic molecules,macromolecules and polymers represent another important approach for the construction of supramolecular architectures with advanced *** this review,we summarize the important contributions made by Chinese researchers in this field,with emphasis on those reported in the past five years.

关键词： host-guest chemistry drug delivery anticancer and antibacterial photodynamic therapy photothermal therapy antidote transmembrane channel bioimaging and biosensing