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SO_(2)-Insertion induced enantioselective oxysulfonylation to access β-chiral sulfones with quaternary carbon stereocenters

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Science China chemistry 2024年第3期67卷 908-913页

作者： Jun Zhang Xuefeng Wang Peiqi Wang Jiayuan Fang Shaoyu Li Jie Wu School of Pharmaceutical and Chemical Engineering&Institute for Advanced Studies Taizhou UniversityShanghai 200438China department of chemistry Fudan UniversityShanghai 200438China State Key Laboratory of Organometallic chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China School of chemistry and Chemical Engineering Henan Normal UniversityXinxiang 453007China

β-Chiral sulfones are structural motifs widely found in natural products and bioactive molecules, while also serving as important intermediates for the synthesis of valuable chiral scaffolds. In contrast to the rapid growth of sulfur dioxide insertion chemistry over the last decade, enantioselective catalytic variants for accessing β-chiral sulfones, especially those bearing a quaternary carbon stereocenter, remain rare. Herein, we report an enantioselective copper/bisoxazoline catalyzed oxysulfonylation of alkenes to yield isoxazolinyl-containing β-chiral sulfones bearing quaternary carbon stereocenters with moderate to excellent yields and up to 96:4 er. The advantage and irreplaceability of this sulfur dioxide insertion catalytic system have been demonstrated by achieving transformations clearly unavailable with the previously reported sulfonyl chloride system. Additionally,the recoverability of the new-developed bisoxazoline ligand L9 and its reusability without any erosion of the catalytic activity and enantioselectivity further demonstrate the usefulness of the protocol.

关键词： β-chiral sulfones sulfur dioxide insertion oxysulfonylation copper catalysis enantioselectivity

Amphiphilic amino-acid derivatives promote gram-scale single-crystal COFs synthesis

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Science China chemistry 2024年第2期67卷 415-416页

作者： Yijia Yuan Kian Ping Loh department of chemistry National University of SingaporeSingapore117543Singapore

Covalent organic frameworks(COFs) are crystalline organic compounds synthesized from covalently linked building blocks that extend in space to form a framework structure with periodic pores. The covalent linkages used... 详细信息

关键词： synthesis correction reversible

Selective control of secondary alcohols upgrading using Ir-catalyzed cross-coupling strategy

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Science China chemistry 2024年第3期67卷 914-921页

作者： Siqi Yang Zeye Lu Jiale Ji Qingshu Zheng Tao Tu Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials Department of ChemistryFudan UniversityShanghai 200438China Frontiers Science Center for Transformative Molecules School of Chemistry and Chemical EngineeringShanghai Jiao Tong UniversityShanghai 200240China State Key Laboratory of Organometallic chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

The selective coupling of alcohols is a fascinating yet challenging approach for upgrading alcohols. Herein, we accomplished the controlled production of β-disubstituted ketones or upgraded secondary alcohols via the Ir-catalyzed cross-coupling of secondary alcohols in excellent yields with broad substrate scopes. This selective control was achieved by using an in-situ generated monoNHC-Ir or a tris-NHC-Ir complex as the catalysts, respectively. Mechanistic studies revealed that the delicate balance between dehydrogenation and hydrogenation abilities of these bifunctional catalysts is crucial for achieving different selectivity. The tris-NHC-Ir complex effectively facilitated dehydrogenation of alcohols and hydrogenation of intermediates, leading to the desired upgraded secondary alcohols. Conversely, the high dehydrogenation ability of the mono-NHC-Ir complex promoted the conversion of formed secondary alcohols back to ketones.

关键词： cross-coupling hydrogen-borrowing NHC-Ir complexes selectivity control upgrading of alcohols

Encapsulated Fe(IV)Molecular Complex for Photoacoustic Imaging

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CCS chemistry 2024年第5期6卷 1184-1197页

作者： Ye Xu Chao Li Zhong-Yu Yu Jiamin Wang Zhaoyang Liu Chao Jiang Zhen-Feng Chen Xiaoyu Wu Ming-Xing Li Hong Yang Zhao-Xi Wang Jonathan L.Sessler department of chemistry Center for Supramolecular Chemistry and CatalysisInnovative Drug Research CenterShanghai UniversityShanghai 200444 College of chemistry and Materials Science Shanghai Key Laboratory of Rare Earth Functional MaterialsShanghai Frontiers Science Center of Biomimetic CatalysisShanghai Normal UniversityShanghai 200234 Sijing Community Health Service Center of Songjiang District Shanghai 201601 Key Laboratory for chemistry and Molecular Engineering of medicinal Resources Guangxi Normal UniversityGuilin 541004 department of chemistry The University of Texas at AustinAustinTexas 78712-1224

stable neutral Fe(IV)complex(Fe-HDCL),readily accessible on the g scale,was found to possess high water solubility and good stability(<5%degradation over 4 h upon photoirradiation).Fe-HDCL is green and absorbs light effectively in the visible region(500–800 nm)with aλmax at 650 nm(ɛ=7830 M^(−1)cm^(−1)).Fe-HDCL also exhibits photothermal(PT)behavior comparable to single-wall carbon nanotubes in the solid *** aqueous solution,high PT conversion(η=72.6%)is achieved,and a strong hyperthermia-based inhibition of cell growth is observed upon subjecting Fe-HDCL to near-infrared 730 nm laser *** biological studies in vitro and in vivo confirmed that Fe-HDCL is biocompatible,clears readily,and allows the visual detection of blood *** subjecting mice to intravenous injection at low doses(e.g.,50μmol·kg^(−1)),Fe-HDCL also permits the photoacoustic(PA)imaging of kidneys and the evaluation of renal fibrosis in mouse *** addition,Fe-HDCL allows PA-based imaging of brain tissues,presumably reflecting its ability to pass through the blood-brain *** thus propose that Fe-HDCL has a role to play as PT agent and as a photodiagnostic.

关键词： stable Fe(IV)complex blood-brain barrier molecular cage photoacoustic imaging renal fibrosis

Dimensional regulation in gigantic molybdenum blue wheels featuring{(W)Mo5}motifs for enhanced proton conductivity

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Nano Research 2024年第9期17卷 8261-8268页

作者： Yu-Lun Wu Jing Du Hai-Ying Zhang Ming-Jun Hou Qiao-Yue Li Wei-Chao Chen Kui-Zhan Shao Bo Zhu Chao Qin Xin-Long Wang Zhong-Min Su Key Laboratory of Polyoxometalate and Reticular Material chemistry of Ministry of Education Department of ChemistryNortheast Normal UniversityChangchun 130024China Hebei Key Laboratory of Organic Functional Molecules National Demonstration Center for Experimental Chemistry EducationTesting and Analysis CenterCollege of Chemistry and Materials ScienceHebei Normal UniversityShijiazhuang 050024China State Key Laboratory of Supramolecular Structure and Materials Institute of Theoretical ChemistryCollege of ChemistryJilin UniversityChangchun 130021China

Dimensional regulation in polyoxometalates is an effective strategy during the design and synthesis of polyoxometalates-based high proton conductors,but it is not available to ***,the precise regulation of dimensionality has been realized in an unprecedented gigantic molybdenum blue wheel family featuring pentagonal{(W)Mo5}motifs through optimizing the molar ratio of Mo/W,including[Gd_(2)Mo_(124)W_(14)O_(422)(H_(2)O)62]38-(0D-{Mo_(124)W_(14)},1),[Mo_(126)W_(14)O441(H_(2)O)51]^(70-)(1D-{Mo_(126)W_(14)}n,2),and[Mo_(124)W_(14)O_(430)(H_(2)O)50]60-(2D-{Mo_(124)W_(14)}n,3).Such important{(W)Mo5}structural motif brings new reactivity into gigantic Mo blue *** are different numbers and sites of{Mo2}defects in each wheel-shaped monomer in 1-3,which leads to the monomers of 2 and 3 to form 1D and 2D architectures via Mo-O-Mo covalent bonds driven by{Mo2}-mediated H_(2)O ligands substitution process,respectively,thus achieving the controllable dimensional *** expected,the proton conductivity of 3 is 10 times higher than that of 1 and 1.7 times higher than that of *** continuous proton hopping sites in 2D network are responsible for the enhanced proton conductivity with lower activation *** study highlights that this dimensional regulation approach remains great potential in preparing polyoxometalates-based high proton conductive materials.

关键词： polyoxometalate molybdenum blue wheels Mo/W mixed-addenda polyoxometalates dimensional regulation proton conduction

Molecule aging induced by electron attacking

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Journal of Energy chemistry 2024年第6期93卷 519-525,I0013页

作者： Ping Song Yining Dong Xue Gong Mingbo Ruan Baoxin Ni Xuanhao Mei Kun Jiang Weilin Xu State Key Laboratory of Electroanalytical chemistry and Jilin Province Key Laboratory of Low Carbon Chemical Power Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchun 130022JilinChina School of Applied chemistry and Engineering University of Science and Technology of Chin1Hefei 230026AnhuiChina Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials Collaborative Innovation Center of Chemistry for Energy MaterialsDepartment of ChemistryFudan UniversityShanghai 200438China

Here we propose a new concept of"molecule aging":with some special treatment,a molecule could be"aged"by losing some unknown tiny particles or pieces from atoms in the molecule,Such"aging"or loss of unknown tiny particles does not change apparently its molecular structure or chemical composition,but some physicochemical properties could be changed *** further confirm such"molecule aging"via a long-term electron attacking to age water(H_(2)O)*** IR spectra show no structural difference between the fresh water and the aged one,while the NMR spectra show that the electron attacking can decrease the size of water *** facts indicate that the electron attacking indeed can"affect"the structure of water molecule slightly but without damaging to its basic molecule *** exploration reveals that the hydrogen evolution reaction(HER)activity of the aged water molecule is lower than the fresh water on the same Pt/C *** density functional theory calculations indicate that the shortened O-H bond in H_(2)O indeed can present lower HER activity,so the observed size decrease of water clusters from NMR probably could be attributed to the shortening of O-H bond in water *** results indicate significantly that the molecule aging can produce materials with new functions for new possible applications.

关键词： Aging of molecules Electron attacking Full width at half maxima Hydrogen evolution reaction

S-scheme heterojunction in photocatalytic hydrogen production

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Journal of Materials Science & Technology 2024年第2期169卷 82-104页

作者： Teng Li Noritatsu Tsubaki Zhiliang Jin School of chemistry and Chemical Engineering North Minzu UniversityYinchuan 750021China department of Applied chemistry Graduate School of EngineeringUniversity of ToyamaGofuku 3190Toyama 930-8555Japan

As an ideal secondary energy source,hydrogen has the title of clean energy and the product of its complete combustion is only water,which is not polluting to the *** hydrogen production technology is an environmentally friendly,safe,and low-cost strategy that requires only an inexhaustible amount of solar energy and water as *** paper provides a detailed and detailed review of S-scheme heterojunction photocatalysts for photocatalytic hydrogen production,mainly including TiO_(2)-based,Perovskite-based,CdS-based,Graphitic phase carbon nitride-based,COF-based graphdiyne-based,ZnO-based,and ZnIn_(2)S_(4)-based S-scheme heterojunction *** classification of S-scheme heterojunctions is ***’s more,various characterizations for direct verification of the charge migration mechanism of S-scheme heterojunctions are *** on the present study,the future potential challenges and future research trends for S-scheme heterojunctions in photocatalytic hydrogen evolution technology are pointed out,which provides feasible strategies for the development and design of S-scheme heterojunction photocatalysts in the field of photocatalytic hydrogen evolution.

关键词： S-scheme heterojunction Photocatalysis Charges migration Hydrogen evolution

Differentially-grown cobalt regulators cooperatively involved in the tandem catalysis for high-yield production of second amines

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Nano Research 2024年第4期17卷 2444-2450页

作者： Jinhui Xu Xiao Wang Ying Wang Fei Wang Lingling Zhang Wenjie Cui Shuyan Song Hongjie Zhang State Key Laboratory of Rare Earth Resource Utilization Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchun 130022China School of Applied chemistry and Engineering University of Science and Technology of ChinaHefei 230026China department of chemistry Tsinghua UniversityBeijing 100084China

One-pot tandem catalysis has been regarded as one of the most atomic economic ways to produce secondary amines,the important platform molecules for chemical synthesis and pharmaceutical manufacture,but it is facing serious issues in overall *** promotional effects are highly desired for boosting the activity and regulating the selectivity of conventional tandem *** this work,we report a high-performance tandem catalyst with maximized synergistic effect among each counterpart by preciously manipulating the spatial structure,which involves the active CeO_(2)/Pt component as kernel,the densely-coated N-doped C(NC)layer as selectivity controller,and the differentially-grown Co species as catalytic performance *** comprehensive investigations,the unique growth mechanism and the promotion effect of Co regulators are ***,the surface-landed Co clusters(Cocs)are crucial to selectivity by altering the adsorption configuration of benzylideneaniline ***,the inner Co particles(Cops)are essential for activity by denoting their electrons to neighboring *** from the unique promotion effect,a remarkably-improved catalytic efficiency(100%nitrobenzene conversion with 94%N-benzylaniline selectivity)is achieved at a relatively low temperature of 80℃,which is much better than that of CeO_(2)/Pt(100%nitrobenzene conversion with 12%N-benzylaniline selectivity)and CeO_(2)/Pt/NC(35%nitrobenzene conversion with 94%benzylideneaniline selectivity).

关键词： tandem catalysis CeO_(2) hierarchical structure heterogeneous catalyst dual-site materials

Nickel-catalyzed carbonylative four-component 1,4-dicarbofunctionalization of 1,3-enynes

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Science China chemistry 2024年第6期67卷 2029-2038页

作者： Yan Zhao Qi-Chao Shan Hong Xin Pin Gao Xu Yang Xin-Hua Duan Li-Na Guo department of chemistry School of ChemistryXi’an Key Laboratory of Sustainable Energy Material Chemistry and Engineering Research Center of Energy StorageMaterials and DevicesMinistry of EducationXi’an Jiaotong UniversityXi’an710049China School of Electrical Engineering Xi’an Jiaotong UniversityXi’an710049China

An efficient Ni-catalyzed four-component 1,4-carbocarbonylation of 1,3-enynes with activated alkyl halides and arylboronic acids under atmospheric pressure of CO is *** tuning the electronic and steric effects of alkyl radicals,both electronrich and electron-deficient 1,3-enynes were compatible with this *** protocol features mild conditions,broad substrate scope,excellent functional group compatibility and facile gram-scale synthesis,providing a practical approach to the quaternary carbon center-containing allenyl *** study revealed that the acyl-NiIIspecies plays an important role in both the coupling and the alkyl radical generation processes.

关键词： Ni catalysis four-component 1 4-carbocarbonylation 1 3-enynes

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