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Carbene-catalyzed enantioselective seleno-Michael addition as access to antimicrobial active Se-containing heterocycles

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Science China Chemistry 2024年第7期67卷 2199-2205页

作者： Hongyan Long Sha Zhao Chunyan Jian Xiuli Wu Fengfei Lu Minghong Liao Fengrui Che Xingxing Wu Yonggui Robin Chi State key laboratory of Green pesticide Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationGuizhou UniversityGuiyang 550025China School of Chemistry Chemical Engineeringand BiotechnologyNanyang Technological UniversitySingapore 637371Singapore

Organoseleniums exhibit a diverse set of biological activities that are pivotal for drug discovery and are widely explored in synthetic chemistry and material *** many transformations have been developed for non-enantioselective C–Se bond formations,the catalyst-controlled stereoselective preparation of chiral organoseleniums continues to be of considerable *** particular,there are limited studies on the enantioselective seleno-Michael addition reactions to access chiral selenium functional ***,we disclose a carbene-catalyzed highly enantioselective nucleophilic C–Se bond construction through formal[3+3]annulations between selenocarboxamides and bromoenals,affording seleno-thiazinone products with good yields and excellent *** choice of a weak inorganic base was pivotal to suppressing the unproductive racemization and decomposition of the selenium ***,the catalytically generated chiral selenium-containing heterocyclic products feature remarkable antimicrobial activities that could serve as promising lead scaffolds for further agrochemical development.

关键词： seleno-Michael addition organocatalysis N-heterocyclic carbene seleno-heterocycles antimicrobial activity

Access to Axially Chiral Aryl Aldehydes via Carbene-Catalyzed Nitrile Formation and Desymmetrization Reaction

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Research 2024年第3期2024卷 715-721页

作者： Yuanlin Cai Ya Lv Liangzhen Shu Zhichao Jin Yonggui Robin Chi Tingting Li National key laboratory of Green pesticide Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationGuizhou UniversityGuiyang 550025China School of Chemistry Chemical Engineeringand BiotechnologyNanyang Technological UniversitySingapore 637371Singapore.

An approach utilizing N-heterocyclic carbene for nitrile formation and desymmetrization reaction is developed. The process involves kinetic resolution, with the axially chiral aryl monoaldehydes obtained in moderate yields with excellent optical purities. These axially chiral aryl monoaldehydes can be conveniently transformed into functionalized molecules, showing great potential as catalysts in organic chemistry.

关键词： chemistry. aldehydes chiral

Indole derivatives as agrochemicals:An overview

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Chinese chemical Letters 2024年第7期35卷 66-72页

作者： Ping Sun Yuanqin Huang Shunhong Chen Xining Ma Zhaokai Yang Jian Wu National key laboratory of Green pesticide Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationGuizhou UniversityGuiyang 550025China

Indole is a biologically active compound formed by the fusion of benzene and pyrrole,and it is widely found in natural products and *** to the unique structure and properties of indole,its derivatives often exhibit distinctive physiological activities,which has led to widespread attention in the field of pesticide *** the design strategies and structure-activity relationships(SARs)of compounds is a crucial step in developing novel *** review mainly summarizes indole compounds with plant growth regulating,antiviral,fungicidal,herbicidal,and insecticidal activities,with the aim of providing new insights into the discovery and mechanism of action of novel indole-based pesticides.

关键词： Indole compounds Agrochemicals Biological activity Structure-activity relationship Mechanism of action

Chiral boryl radical catalyzed asymmetric radical cycloisomerization

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Science China Chemistry 2024年第7期67卷 2121-2123页

作者： Jiamiao Jin Shi-Chao Ren Yonggui Robin Chi National key laboratory of Green pesticide Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationGuizhou UniversityGuiyang 550025China School of Chemistry Chemical Engineeringand BiotechnologyNanyang Technological UniversitySingapore 637371Singapore

Asymmetric catalytic organic synthesis is of profound importance in modern research and industries,providing optically enriched molecules with diverse structures and functions[1].Enzymes,transition metal complexes,and simple organic molecules have all been found as powerful catalysts that enable the bond breaking and forming events with excellent control over stereo-selectivity *** the realm of designed small molecule organic catalysts.

关键词： radical catalyzed asymmetric

Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings

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Chinese chemical Letters 2024年第9期35卷 150-154页

作者： Kun Tang Fen Su Shijie Pan Fengfei Lu Zhongfu Luo Fengrui Che Xingxing Wu Yonggui Robin Chi National key laboratory of Green pesticide Key Laboratory of Green Pesticide and Agricultural BioengineeringMinistry of EducationGuizhou UniversityHuaxi DistrictGuiyang 550025China School of chemistry Chemical Engineeringand BiotechnologyNanyang Technological UniversitySingapore 637371Singapore

Enones are widely explored in synthetic chemistry as fundamental building blocks for a wide range of reactions and exhibit intriguing biological activities that are pivotal for drug *** development of synthetic strategies for highly efficient preparation of enones thereby receives intense attention,in particular through the transition metal-catalyzed coupling ***,we describe a carbene-catalyzed cross dehydrogenative coupling(CDC)reaction that enables effective assembly of simple aldehydes and alkenes to afford a diverse set of enone ***,the in situ generated aryl radical is pivotal to“activate”the alkene by forming an allyl radical through intermolecular hydrogen atom transfer(HAT)pathway and thus forging the carbon-carbon bond formation with aldehyde as the acyl ***,our method represents the first example on the enone synthesis through coupling of“non-functionalized”aldehydes and alkenes as coupling partners,and offers a distinct organocatalytic pathway to the transition metal-catalyzed coupling transformations.

关键词： Enones Cross dehydrogenative coupling N-Heterocyclic carbene Aryl radical Hydrogen atom transfer

Symmetry dependent activation and reactivity of peroxysulfates on FeS_(2)(001)surface

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Science Bulletin 2024年第2期69卷 154-158页

作者： Cancan Ling Meiqi Li Hao Li Xiufan Liu Guangming Zhan Hongwei Sun Chuan Liang Yaling Li Bing Zhou Jincai Zhao Lizhi Zhang School of Environmental Science and Engineering Shanghai Jiao Tong UniversityShanghai 200240China key laboratory of pesticide&chemical biology of Ministry of Education Institute of Environmental&Applied ChemistryCentral China Normal UniversityWuhan 430079China

Heterogeneous peroxysulfates-based advanced oxidation processes(AOPs)have garnered significant attention for purifying organic wastewater since they offer many advantages like low cost,safe storage,facile activation and reactive species participation[1].Nonradical and radical pathways have been proposed to be involved in peroxysulfates activation.

关键词： activation radical reactivity

Recent advances in the microfluidic generation of shape-controllable hydrogel microparticles and their applications

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Green chemical Engineering 2024年第1期5卷 16-30页

作者： Yingzhe Liu Zhuo Chen Jianhong Xu The State key lab of chemical Engineering Department of Chemical EngineeringTsinghua UniversityBeijing100084China

Hydrogel microparticles,generally accepted as significant green materials,have been widely used in chemical,biological,and biomedical fields owing to their excellent biocompatibility,biodegradability,and *** these,non-spherical hydrogel microparticles with diverse shape anisotropy have great potential in applications such as drug delivery,cellular interaction,micromotors,*** from their shapes,their functionalities in such fields cannot be satisfied by the typical spherical ***,microfluidics with precise control and domination of fluids at microflow sizes has emerged as a powerful method for synthesizing shape-controllable hydrogel microparticles with good monodispersity and unique *** this review,we tried to provide an overview of the production of non-spherical microparticles composed of green hydrogel materials,emphasizing the microfluidic ***,a brief introduction to their current applications is also presented.

关键词： Microfluidics Hydrogel Microparticles Non-spherical Anisotropic Green materials

Intrinsic pentagon defect engineering in multiple spatial-scale carbon frameworks for efficient triiodide reduction

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Journal of Energy Chemistry 2024年第8期95卷 20-28,I0002页

作者： Siyi Hou Xuedan Song Chang Yu Jiangwei Chang Yiwang Ding Yingbin Liu Xiubo Zhang Weizhe Liu Jieshan Qiu State key lab of Fine chemicals Liaoning Key Lab for Energy Materials and Chemical EngineeringFrontier Science Center for Smart MaterialsSchool of Chemical EngineeringDalian University of TechnologyDalian 116024LiaoningChina Liaoning key lab for Energy Materials and chemical Engineering Frontier Science Center for Smart MaterialsSchool of ChemistryDalian University of TechnologyDalian 116024LiaoningChina State key laboratory of chemical Resource Engineering College of Chemical EngineeringBeijing University of Chemical TechnologyBeijing 100029China

Intrinsic topological defect engineering has been proven as a promising strategy to elevate the electrocatalytic activity of carbon ***,the controllable construction of high-density and specific topological defects in carbon frameworks to reveal the relationship between reactivity and defect structure remains a challenging ***,the intrinsic pentagon carbon sites that can favor electron overflow and enhance their binding affinity towards the intermediates of catalytic reaction are firstly presented by the work function and the p-band center *** experimentally verify this,the cage-opening reaction of fullerene is proposed and utilized for synthesizing carbon quantum dots with specific pentagon configuration(CQDs-P),subsequently utilizing CQDs-P to modulate the micro-scale defect density of three-dimensional reduced graphene oxide(rGO)viaπ-π*** multiple spatial-scale rGO-conjugated CQDs-P structure simultaneously possesses abundant pentagon and edge defects as catalytic active sites and long-range-orderedπelectron delocalization system as conductive *** defects-rich CQDs-P/rGO-4 all-carbon-based catalyst exhibits superb catalytic activity for triiodide reduction reaction with a high photoelectric conversion efficiency of 8.40%,superior to the Pt reference(7.97%).Theoretical calculations suggest that pentagon defects in the carbon frameworks can promote charge transfer and modulate the adsorption/dissociation behavior of the reaction intermediates,thus enhancing the electrocatalytic activity of the *** work confirms the role of intrinsic pentagon defects in catalytic reactions and provides a new insight into the synthesis of defects-rich carbon catalysts.

关键词： Defect engineering Pentagon carbon Carbon quantum dots Electrocatalytic activity Triiodide reduction

An effective'salt in dimethyl sulfoxide/water'electrolyte enables high-voltage supercapacitor operated at-50℃

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Journal of Energy Chemistry 2024年第6期93卷 361-367,I0009页

作者： Yingbin Liu Chang Yu Xuedan Song Siyi Hou Shuqin Lan Jinhe Yu Yuanyang Xie Jieshan Qiu State key lab of Fine chemicals Frontier Science Center for Smart MaterialsSchool of Chemical EngineeringLiaoning Key Lab for Energy Materials and Chemical EngineeringDalian University of TechnologyDalian 116024LiaoningChina School of Chemistry Frontier Science Center for Smart MaterialsLiaoning Key Lab for Energy Materials and Chemical EngineeringDalian University of TechnologyDalian 116024LiaoningChina College of chemical Engineering State Key Laboratory of Chemical Resource EngineeringBeijing University of Chemical TechnologyBeijing 100029China

Compared with organic electrolytes,aqueous electrolytes exhibit significantly higher ionic conductivity and possess inherent safety features,showcasing unique advantages in ***,challenges remain for low-salt aqueous electrolytes operating at high voltage and low ***,we report a low-salt(0.87 m,m means mol kg^(-1))'salt in dimethyl sulfoxide/water'hybrid electrolyte with non-flammability via hybridizing aqueous electrolyte with an organic co-solvent of dimethyl sulfoxide(hydrogen bond acceptor).As a result,the 0.87 m hybrid electrolyte exhibits enhanced electrochemical stability,a freezing temperature below-50℃,and an outstanding ionic conductivity of 0.52mS cm~(-1)at-50℃.Dimethyl sulfoxide can anchor water molecules through intermolecular hydrogen bond interaction,effectively reinforcing the stability of water in the hybrid ***,the interaction between dimethyl sulfoxide and water molecules diminishes the involvement of water in the generation of ordered ice crystals,finally facilitating the low-temperature performance of the hybrid *** paired with the 0.87 m'salt in dimethyl sulfoxide/water'hybrid electrolyte,the symmetric supercapacitor presents a 2.0 V high operating voltage at 25℃,and can operate stably at-50℃.Importantly,the suppressed electrochemical reaction of water at-50℃further leads to the symmetric supercapacitor operated at a higher voltage of 2.6 *** modification strategy opens an effective avenue to develop low-salt electrolytes for high-voltage and low-temperature aqueous supercapacitors.

关键词： Dimethyl sulfoxide Co-solvent High voltage Low temperature Supercapacitors