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From aniline to phenol: carbon-nitrogen bond activation via uranyl photoredox catalysis

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National Science Review 2022年第6期9卷 74-80页

作者： Deqing Hu Yilin Zhou Xuefeng Jiang Shanghai Key Laboratory of Green Chemistry and Chemical Process School of Chemistry and Molecular Engineering East China Normal University State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences State Key Laboratory of Elemento-Organic Chemistry Nankai University

Carbon-nitrogen bond activation, via uranyl photoredox catalysis with water, enabled the conversion of 40 protogenetic anilines, 8 N-substituted anilines and 9 aniline-containing natural products/pharmaceuticals to the corresponding phenols in an ambient environment. A single-electron transfer process between a protonated aniline and uranyl catalyst, which was disclosed by radical quenching experiments and Stern-Volmer analysis, facilitated the following oxygen atom transfer process between the radical cation of protonated anilines and uranyl peroxide originating from water-splitting.18O labeling and15N tracking unambiguously depicted that the oxygen came from water and amino group left as ammonium salt. The 100-fold efficiency of the flow operation demonstrated the great potential of the conversion process for industrial synthetic application.

关键词： C−N bond activation C−O bond formation uranyl cations photoredox catalysis

Advances in the construction of diverse SuFEx linkers

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National Science Review 2023年第6期10卷 226-244页

作者： Daming Zeng Wei-Ping Deng Xuefeng Jiang Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism School of Pharmacy East China University of Science and Technology Shanghai Key Laboratory of Green Chemistry and Chemical Process School of Chemistry and Molecular Engineering East China Normal University

Sulfur fluoride exchange(SuFEx),a new generation of click chemistry,was first presented by Sharpless,Dong and co-workers in 2014.Owing to the high stability and yet efficient reactivity of the SⅥ-F bond,SuFEx has found widespread applications in organic synthesis,materials science,chemical biology and drug discovery.A diverse collection of SuFEx linkers has emerged,involving gaseous SO2F2and SOF4hubs;SOF4-derived iminosulfur oxydifluorides;O-,N-and C-attached sulfonyl fluorides and sulfonimidoyl fluorides;and novel sulfondiimidoyl fluorides.This review summarizes the progress of these SuFEx connectors,with an emphasis on analysing the advantages and disadvantages of synthetic strategies of these connectors based on the SuFEx concept,and it is expected to be beneficial to researchers to rapidly and correctly understand this field,thus inspiring further development in SuFEx chemistry.

关键词： SuFEx SuFEx linker SVI–F bond synthetic strategy

Optothermal dynamics in whispering-gallery microresonators

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Light(Science & Applications) 2020年第1期9卷 1760-1774页

作者： Xuefeng Jiang Lan Yang Department of Electrical and System Engineering Washington University in St.LouisSt.LouisMO 63130USA

Optical whispering-gallery-mode microresonators with ultrahigh quality factors and small mode volumes have played an important role in modern physics.They have been demonstrated as a diverse platform for a wide range of applications in photonics,such as nonlinear optics,optomechanics,quantum optics,and information processing.Thermal behaviors induced by power build-up in the resonators or environmental perturbations are ubiquitous in high-quality-factor whispering-gallery-mode resonators and have played an important role in their operation for various applications.In this review,we discuss the mechanisms of laser-field-induced thermal nonlinear effects,including thermal bistability and thermal oscillation.With the help of the thermal bistability effect,optothermal spectroscopy and optical nonreciprocity have been demonstrated.By tuning the temperature of the environment,the resonant mode frequency will shift,which can also be used for thermal sensing/tuning applications.The thermal locking technique and thermal imaging mechanisms are discussed briefly.Finally,we review some techniques employed to achieve thermal stability in a high-quality-factor resonator system.

关键词： oscillation optics nonlinear

Straightforward Sulfonamidation via Metabisulfite-Mediated CrossCoupling of Nitroarenes and Boronic Acids under Transition-Metal-Free Conditionst

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Chinese Journal of Chemistry 2020年第12期38卷 1521-1525页

作者： Yaping Li Ming Wang Xuefeng Jiang Shanghai Key Laboratory of Green Chemistry and Chemical Process School of Chemistry and Molecular EngineeringEast China Norm al University3663 North Zhongshan RoadShanghai 200062China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of Sciences345 Lingling RoadShanghai 200032China

of main observation and conclusion A straightforward multicomponent sufonamidation of nitroarenes,sodium metabisulfite and boronicacids was established under transition-mnetal-free conditions to access diverse sulfonamides from readily avilable and low-cost materials modularv.Inorganic salt sodium metabisulfite not only served as a sulfur dioxide source,but also played a key role for both activator and reductant duringsulfonamidation.Notably,naturlly occuring biomolecules and pharmaceuticals with multiple heteroatorms and sensitive functional groups were intensivly investigated in this transformtion providing versatile sulionamides collectively,further mechanistic studies demonstrated that nitrosoarene is thekey intermediate,and the activation of boronic acid is the rate-determining step in the transformation.

关键词： boron Transition straight

Full-Spectrum Fluoromethyl Sulfonation via Modularized Multicomponent Coupling

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CCS Chemistry 2022年第5期4卷 1526-1534页

作者： Kejie Li Ming Wang Xuefeng Jiang Shanghai Key Laboratory of Green Chemistry and Chemical Process School of Chemistry and Molecular EngineeringEast China Normal UniversityShanghai 200062 State Key Laboratory of Elemento-Organic Chemistry Nankai UniversityTianjin 300071

Modular free-assembly construction of mono-,di-,and tri-fluoromethyl sulfones was comprehensively achieved by a combination of halides,a sulfur dioxide surrogate,and halofluorocarbons.The industrial raw material thiourea dioxide served as the sulfur dioxide source,combined with readily available fluorocarbon sources such as 2-bromo-2-fluoroacetate and chlorodifluoromethane(ClCF_(2)H,Freon)employed as fluoromethyl reagents.Notably,four methyl sulfone-containing pharmaceuticals were modified into three types of fluoromethyl sulfones,displaying their great potential for drug discovery via the current strategy.Mechanistic studies further demonstrated that C-F…H-N interactions between thiourea dioxide and halofluorocarbons play a key role in stabilizing monofluoromethyl electrophiles and difluorocarbene species.

关键词： sulfone trifluoromethyl sulfone difluoromethyl sulfone monofluoromethyl sulfone thiourea dioxide

Pd-Catalyzed C-S Cyclization via C-H Functionalization Strategy： Access to Sulfur-containing Benzoheterocyclics

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Chinese Journal of Chemistry 2018年第10期36卷 921-924页

作者： Shihao then Ming Wang Xuefeng Jiang Shanghai Key Laboratory of Green Chemistry and Chemical Process School of Chemistry and Molecular Engineering East China Normal Uni- versity 3663 North Zhongshan Road Shanghai 200062 China State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 345 Lingling Road Shanghai 200032 China

A C-H sulfurated cyclization protocol starting from thioacetates is developed for straightforward construction of sulfur-containing benzo- heterocyclics. The diversiform functional dihydrobenzothiophenes and thiochromans were comprehensively achieved through the Pd-catalyzed carbon- sulfur cyclization. Mechanistic studies indicated that C-H bond cleavage was involved in the rate-determining step. [1]Benzothieno-[3,2-b]- [1]benzothiophene （BTBT） and benzo[b]thieno[2,3-d]thiophene （BTT） were efficiently established as the well-known organic field-effect transistor （OFET） material molecules through this methodology.

关键词： C-S cyclization C-H functionalization dihydrobenzothiophene thiochromans palladium

The application of sulfur-containing peptides in drug discovery

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Chinese Chemical Letters 2018年第7期29卷 1079-1087页

作者： Jiaoyan Zhao Xuefeng Jiang Shanghai Key Laboratory of Green Chemistry and Chemical Process School of Chemistry and Molecular EngineeringEast China Normal University State Key Laboratory of Elemento-organic Chemistry Nankai University

In recent decades, peptides as potential drugs were more and more explored with the development of non-oral medicine. There into, sulfur-containing peptide is one of the most popular aspects in peptide drugs due to the introduction of sulfur atoms leading unique properties.The purpose of the present review is to focus on the discovery of various sulfur-containing peptides with particular emphasis on their pharmacological mechanisms. This review is organized according to the structures of the sulfurcontaining peptides.

关键词： Peptides Disulfide Thioether Thiazole Drug discovery

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Research strategies in click chemistry: Measuring its cognitive contents and knowledge flow

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Chinese Chemical Letters 2023年第2期34卷 3-6页

作者： Jing Zhu Ming Chen He Liang Quanmin Li Xuefeng Jiang Department of Philosophy East China Normal UniversityShanghai 200241China School of Journalism Fudan UniversityShanghai 200433China Shanghai Key Laboratory of Green Chemistry and Chemical Process Department of ChemistryEast China Normal UniversityShanghai 200062China

The issue about how outstanding scientists obtained innovative findings has drawn the interest of researchers in science, policy and scientometrics. Here, we attempt to address this question by using computational methods to measure the cognitive content and concepts of K. Barry Sharpless’ research and estimate the knowledge flow of his click chemistry to other fields. First, we traced Sharpless’ conceptual journey over time through topic modeling approach, mapping and clustering of the epistemic network from distant reading his publications. We find that connectivity and functions, the core features of click chemistry, are embodied in his constant search for simplicity. What makes simplicity possible is his continuous work with collaborators on reactivity and reaction mechanisms. Moreover, citation and link analysis show that click chemistry had a much richer impact on other research fields than what is generally acknowledged, and drew solutions to significant and practical questions back to chemistry from biology.Together with these findings, we propose that the click chemistry philosophy follows the way that values nature’s principle. Chemistry has a clear-cut epistemic domain in modeling Nature. Thus, click chemistry as a concept on doing science beyond a connective technology goes across the boundaries between disciplines and impacts many other fields.

关键词： Click chemistry K.B.Sharpless Research strategies Connectivity History and philosophy of chemistry

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FeS@LAB-35@Ti_(3)C_(2)as a high-efficiency nanozyme for near infrared light induced photothermal enhanced chemodynamic antibacterial activity and wound healing

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Nano Research 2023年第2期16卷 2840-2850页

作者： Gaoqi Sun Xuefeng Jiang Cheng Liu Saijie Song Jun Zhang Jian Shen National and Local Joint Engineering Research Center of Biomedical Functional Materials School of Chemistry and Materials ScienceNanjing Normal UniversityNanjing 210023China Medical School Nanjing UniversityNanjing 210093China jiangsu Engineering Research Center of Interfacial Chemistry Nanjing UniversityNanjing 210023China

The abuse of antibiotics leads to a significant increase in bacterial resistance,which makes it difficult to treat bacterial infections.Therefore,it is urgent to develop new strategies for efficient antibacterial and wound healing.Recently,nanozymes based antibacterial agents have attracted increasing attention for their multifunction and high efficiency.In this study,we report a FeS@lauramidopropyl betaine(LAB-35)@Ti_(3)C_(2)nanozyme as a high-efficiency antibacterial agent for near infrared(NIR)light induced photothermal enhanced chemodynamic antibacteria and wound healing.The FeS@LAB-35@Ti_(3)C_(2)nanozyme possesses peroxidase-like catalysis activity,which can promote the generation of hydroxyl radicals(·OH)through catalyzing the decomposition of H_(2)O_(2).FeS@LAB-35@Ti_(3)C_(2)has photothermal conversion efficiency(η=65.1%),and it exhibits enhanced catalytic activity under NIR light irradiation.The in vitro antibacterial experiments demonstrate the excellent antibacterial activity of FeS@LAB-35@Ti_(3)C_(2)against representative Gram-negative Escherichia coli and Gram-positive Staphylococcus aureus.The animal experiments indicate that FeS@LAB-35@Ti_(3)C_(2)nanozyme can effectively inhibit wound ulceration and promote wound healing.Overall,this study proposes FeS@LAB-35@Ti_(3)C_(2)nanozyme that integrates chemodynamic and photothermal therapy,which provides an efficient strategy for bacterial inhibition and wound healing.

关键词： MXene FeS nanozyme photothermal enhanced chemodynamic antibacterial activity wound healing