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A general method for one-step synthesis of monofluoroiodane(Ⅲ)reagents using silver difluoride

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Chinese Chemical Letters 2022年第11期33卷 4834-4837页

作者： Jing Ren Meng-Cheng Jia Feng-Huan Du Chi Zhang State Key Laboratory of Elemento-Organic Chemistry The Research Institute of Elemento-Organic ChemistryCollege of ChemistryNankai UniversityTianjin 300071China

Herein we report a new general method for one-step synthesis of four kinds of fluoroiodane(Ⅲ)reagents by treating the corresponding aryl iodides with silver difluoride(AgF_(2)).This is the first method applicable for the synthesis of all four fluoroiodane(Ⅲ)reagents including p-iodotoluene difluoride(1),fluoro-benziodoxole(2),fluoro-benziodoxolone(3),and fluoro-N-acetylbenziodazole(4).AgF_(2)was firstly employed in the direct oxidative fluorination of iodobenzene and thus has shown its outstanding oxidation and fluorine-transfer ability.The use of AgF_(2)has improved the synthesis of fluoroiodane(Ⅲ)reagents by shortening the reaction steps,avoiding the use of hazardous reagents,and simplifying the experimental operations.It was worth noting that we have developed the first one-step direct synthetic method for 3,while 3 can only be synthesized through Cl→F ligand exchange reaction previously.

关键词： Monofluoroiodane(Ⅲ)reagents Silver difluoride Iodobenzene derivatives One-step synthesis DFT calculations

Palladium-Catalyzed Skeletal Reorganization of Cyclobutanones Invoving Successive C—C Bond/C—H Bond Cleavage

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中国化学:英文版 2023年第14期41卷 1679-1683页

作者： Ruirui Li Xiaonan Shi Dongbing Zhao state key laboratory and Institute of elemento-organic chemistry College of ChemistryNankai UniversityTianjin300071 China

The utilization of cyclobutanones as the synthon in transition metal catalysis has been made great success.Because C(carbonyl)−C bond of cyclobutanones can be cleaved through strain release.Despite those advancements,the main catalysts in literature are Rh catalysts or Ni catalysts and the reaction with C—H bond is still underdeveloped.Herein,we realized the first palladium-catalyzed skeletal reorganization of cyclobutanones involving successive cleavage of C(carbonyl)−C bonds and C—H bond cleavage,which constitutes an rapid access to diverse indanones.In contrast to the previous Rh-catalytic system,the Pd-catalytic system herein involves different mechanism and features several advantages:1)no need of directing group to facilitate the C(carbonyl)−C bond cleavage;2)much milder reaction condition and 3)simplified work-up.

关键词： Cyclobutanones C-C activation C-H activation Palladium catalysis Ring expansion

In situ crosslink polymerization induced long-lived multicolor supramolecular hydrogel based on modifiedβ-cyclodextrin

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Chinese Chemical Letters 2024年第2期35卷 374-379页

作者： Yonghui Sun Linnan Jiang Yong Chen Yu Liu College of chemistry State Key Laboratory of Elemento-Organic Chemistry Nankai UniversityTianjin 300071China

The construction of hydrogels with good mechanical properties and phosphorescent properties is full of challenges.Herein,we report a supramolecular phosphorescent hydrogel with long lifetime,high tensile strength and self-healing property,which can be easily constructed through in-situ thermalinitiated polymerization of isocyanatoethyl acrylate-modifiedβ-cyclodextrin(β-CD-DA)and acrylatemodified adamantane(Ad-DA),acrylic acid(AA),followed by the non-covalent association with carbon dots(CNDs).The lifetime of phosphorescent hydrogel can reach 1261 ms at room temperature,and the quantum yield is 11%.Importantly,through the efficient triplet to singlet Förster resonance energy transfer(TS-FRET),the phosphorescent hydrogel shows the good phosphorescence energy transfer property for organic dyes Rhodamine B and Eosin Y with the delayed fluorescence lifetime up to 730 ms and 585 ms as well as the energy transfer efficiency(Φ_(ET))up to 99.9%and 99.3%,respectively.Moreover,owing to the host-guest interactions betweenβ-CD-DA and Ad-DA,the three-dimensional cross-linked network phosphorescent hydrogel can be easily stretched to 18 times of its original length,and can achieve self-healing of the cut surfaces within 30 min.These results will expand the scope of phosphorescent materials and provide new ideas and opportunities for materials science.

关键词： Room temperature phosphorescence Hydrogel Phosphorescence energy transfer Cyclodextrin Supramolecular interaction

Synthesis of 2-Deoxy-C-Glycosides via Iridium-Catalyzed sp^(2)and sp^(3)C-H Glycosylation with Unfunctionalized Glycals

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Chinese Journal of chemistry 2022年第5期40卷 571-576页

作者： Wanjun Zhu Qikai Sun Hai Chang Hui-Xing Zhang Quanquan Wang Gong Chen Gang He state key laboratory and Institute of elemento-organic chemistry College of ChemistryNankai UniversityTianjin300071 China

A new protocol for the synthesis of 2-deoxy-C-aryl-glycosides and 2-deoxy-C-alkyl-glycosides via iridium-catalyzed directed C—H glycosylation with glycals is reported.The method is amenable for both the C_(2)C—H glycosylation of indoles and the methyl C—H glycosylation of secondary methyl amines under the control of an N-linked benzoxazole directing group.The benzoxazole group can be cleanly removed by the treatment of KOH or LiAlH_(4).

关键词： 2-Deoxy-C-glycoside Iridium C-Hactivation Glycosylation Glycals

Fluorescence Sensing of Glutathione Thiyl Radical by BODIPY-Modified β-Cyclodextrin

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Chinese Journal of chemistry 2022年第4期40卷 493-499页

作者： Zhixue Liu Xianyin Dai Qiaoyan Xu Xiaohan Sun Yu Liu College of chemistry State Key Laboratory of Elemento-Organic ChemistryNankai UniversityTianjin 300071China

Comprehensive Summary The fluorescence sensing of intracellular glutathione thiyl radical(GS·)is in great demand to seek the GS·-related pathophysiological events.Herein,boron-dipyrromethene(BODIPY)-modified β-cyclodextrin was developed for high-efficiency sensing of GS·,accompanied by a fast response time(t_(1/2)=218 s),with the detection limit of 468 nmol/L.Cell experiments indicated that the BODIPY-modified p-cyclodextrin could be applied to detect the GS· in live A549 cells.

关键词： Cyclodextrins Glutathione thiyl radical Biosensors BODIPY Radical reaction

Electro-reductive C-H cyanoalkylation of quinoxalin-2(1H)-ones

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Chinese Chemical Letters 2022年第8期33卷 4057-4060页

作者： Ling Ding Kaikai Niu Yuxiu Liu Qingmin Wang State Key Laboratory of Elemento-Organic Chemistry Research Institute of Elemento-Organic ChemistryCollege of ChemistryFrontiers Science Center for New Organic MatterNankai UniversityTianjin 300071China

Herein,we report a practical electro-reductive protocol for the direct C-H cyanoalkylation of quinoxalin-2(1 H)-ones via iminyl radical-mediated ring opening.These mild reactions proceed under metal-,reductant-,and re... 详细信息

关键词： Electro-reductive C-H cyanoalkylation Reductant-free Quinoxalin-2(1H)-ones Ring-opening

Synthesis and insecticidal evaluation of novel sulfide-containing amide derivatives as potential ryanodine receptor modulators

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Chinese Chemical Letters 2022年第1期33卷 501-507页

作者： Yan Zhang Yuxin Li Huan Li Junfeng Shang Zhengming Li Baolei Wang State Key Laboratory of Elemento-Organic Chemistry College of ChemistryNankai UniversityTianjin 300071China

With the aim of discovering new bioactive pesticides for crop protection,a series of novel sulfidecontaining amide derivatives A were efficiently synthesized via a strategy of modifying the“amide”structure of anthranilic diamide insecticides.The single-crystal structures of A2-3 and A4-5 were firstly reported.The bioassay results showed that most of the synthesized compounds display moderate to high insecticidal activities.Particularly,some sulfone-containing compounds,e.g.,A2-3,A3-3 and A6-3,not only possessed favorable lethality rate(50%–100%)against P.xylostella at a concentration of 0.1 mg/L,but also held good activities towards a variety of agricultural pests such as M.separata,C.pipiens pallen,H.armigera and O.nubilalis;the larvicidal activities of A4-1 and A6-1 towards P.xylostella were close to that of chlorantraniliprole at 0.01 mg/L.The calcium imaging experiments revealed that the representative compounds A2-3 and A6-3 are potential ryanodine receptor(RyR)modulators.The structure–activity relationships were discussed in detail.These results provide useful information for further design and development of novel insecticides.

关键词： Sulfide-containing amide derivatives Sulfoxide Sulfone Insecticidal activities Calcium channel

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

Lighting up nonbenzenoid acepleiadylene with ultra-narrowband emission through aromaticity modulation

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Science China chemistry 2023年第12期66卷 3506-3510页

作者： Pengcai Liu Xiao-Yu Tang Cheng-Zhuo Du Rui Xue Xing-Yu Chen Jiawen Cao Xiao-Ye Wang State Key Laboratory of Elemento-Organic Chemistry Frontiers Science Center for New Organic MatterCollege of ChemistryNankai UniversityTianjin 300071China

Nonbenzenoid polycyclic arenes have attracted great attention because of their unique topological structures and appealing properties;however,they are generally considered as poor luminescent materials due to the ring puckering behavior of the nonhexagons.Acepleiadylene(APD),a nonbenzenoid isomer of pyrene,has been demonstrated as an excellent building block for optoelectronic applications,but its poor photoluminescence quantum yield(PLQY)has hampered its application in luminescent materials.Considering that the ring puckering character can be suppressed by increasing the rigidity of the nonhexagon rings,herein,we propose a novel strategy for enhancing the aromaticity of the nonhexagons to improve the PLQYs of APD derivatives.Electron-withdrawing cyano groups are introduced on the five-membered ring of APD to enhance the chargeseparated character and thus the aromaticity of the nonhexagons,endowing the cyano-substituted APDs(CNAPD and 2CNAPD)with better rigidity.Therefore,the cyano substitution successfully suppresses the nonradiative energy dissipation caused by the ring puckering,improving the PLQY from 2.4%for APD to 14%for CNAPD,and to 63%for 2CNAPD.In addition,the enhanced rigidity also suppresses the vibration sideband of the photoluminescence spectra,leading to an ultra-narrowband emission from 2CNAPD with a full-width at half-maximum(FWHM)of 13 nm(47 me V),which is a new record in organic molecules.These results demonstrate that APD derivatives have great potential in highly efficient luminescent materials with high color purity via the aromaticity regulation strategy,which provides a novel concept for designing nonbenzenoid luminescent materials.

关键词： nonbenzenoid arenes luminescence narrowband emission acepleiadylene