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Carbon Monoxide as C1 Building Block in Fine Chemical Synthesis

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Chinese Journal of chemistry 2024年第2期42卷 199-221页

作者： Rui M.B.Carrilho Mario J.F.Calvete Gabor Mikle Laszlo Kollar Mariette M.Pereira University of Coimbra Coimbra Chemistry CentreDepartment of ChemistryRua Larga3004-535 CoimbraPortugal department of General and Inorganic chemistry and ELKH-PTE Research Groupfor Selective Chemical Syntheses University of PecsIfjusag utja 6H-7624 PecsHungary

Carbon monoxide(CO)has become one of the most relevant and versatile renewable C1 building blocks for chemical synthesis,especially in the fine chemicals industry,due to the development of efficient and selective catalysts for its *** this review,we present a comprehensive critical analysis of the last 10 years literature on the use of CO as a renewable feedstock for fine chemicals *** review is organized by type of catalytic reaction,namely alkene and alkyne carbonylation,hydroformylation,carbonylation of aryl halides,carbonylative cross-coupling and C-H *** examples of the synthesis of relevant building blocks and/or known pharmaceuticals are *** is placed on examples of utilizing CO as the C1 building block in one or more catalytic *** catalyst used and the reaction conditions are consistently presented throughout all of the examples.

关键词： Carbon monoxide Fine chemicals Carbonylation Hydroformylation C-H functionalization

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

Spin chiral anisotropy of diamagnetic chiral mesostructured In_(2)O_(3) films

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Nano Research 2024年第8期17卷 7756-7761页

作者： Ting Ji Quanzheng Deng Hao Chen Lu Han Zhibei Qu Shunai Che Yingying Duan Frontiers Science Center for Transformative Molecules State Key Laboratory of Metal Matrix CompositesShanghai Key Laboratory for Molecular Engineering of Chiral DrugsSchool of Chemistry and Chemical EngineeringShanghai Jiao Tong UniversityShanghai 200240China School of Chemical Science and Engineering Tongji UniversityShanghai 200092China department of medicinal chemistry School of PharmacyFudan UniversityShanghai 201203China

Spin chiral anisotropy(SChA)refers to the occurrence of different spin polarization in antipodal chiral ***,we report the SChA in diamagnetic chiral mesostructured In2O3 films(CMIFs)with manifestation of chirality-dependent magnetic circular dichroism(MCD)*** were grown on fluorine-doped tin dioxide conductive glass(FTO)substrates,which were synthesized via a hydrothermal route,with malic acid used as the symmetry-breaking *** levels of chirality have been identified in CMIFs:primary nanoflakes with atomically twisted crystal lattices and secondary helical stacking of the *** exhibit chirality-dependent asymmetric MCD signals due to the different interactions of chirality-induced effective magnetic field and external magnetic field,which distinguish from the commonly observed external magnetic fielddependent symmetric MCD *** findings provide insights into spin manipulation of spin-paired diamagnets.

关键词： chiral inorganics mesostructure diamagnet spin chiral anisotropy(SChA) magnetic circular dichroism(MCD)

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

Furfural residues derived nitrogen-sulfur co-doped sheet-like carbon: An excellent electrode for dual carbon lithium-ion capacitors

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Green Energy & Environment 2024年第9期9卷 1427-1439页

作者： Xiaoying Guo Yan Qiao Zonglin Yi Christian Marcus Pedersen Yingxiong Wang Xiaodong Tian Peide Han College of Materials Science and Engineering Taiyuan University of Technology State Key Laboratory of Coal Conversion Institute of Coal Chemistry Chinese Academy of Sciences University of Chinese Academy of Sciences CAS Key Laboratory of Carbon Materials Institute of Coal Chemistry Chinese Academy of Sciences department of chemistry University of Copenhagen Universitetsparken 5 College of chemistry Taiyuan University of Technology

The state-of-the-art lithium-ion capacitors （LICs）,consisting of high-capacity battery-type anode and high-rate capacitor-type cathode,can deliver high energy density and large power density when comparing with traditional supercapacitors and lithium-ion batteries,***,the ion kinetics mismatch between cathode and anode leads to unsatisfied cycling lifetime and anode *** efforts have been devoted to solving the abovementioned *** promising strategy is altering high conductive hard carbon anode with excellent structural stability to match with activated carbon cathode,assembling dual-carbon *** this contribution,one-pot in-situ expansion and heteroatom doping strategy was adopted to prepare sheet-like hard carbon,while activated carbon was obtained involving *** persulfate was used as expanding and doping agent *** furfural residues （FR） were served as carbon *** resulting hard carbon （FRNS-HC） and activated carbon （FRNS-AC）show excellent electrochemical performance as negative and positive electrodes in a lithium-ion battery （LIB）.To be specific,374.2 m Ah g-1and 123.1 m Ah g-1can be achieved at 0.1 A g-1and 5 A g-1when FRNS-HC was tested as *** combined with a highly porous carbon cathode (SBET=2961 m2g-1) synthesized from the same precursor,the LIC showed high specific energy of147.67 Wh kg-1at approximately 199.93 W kg-1,and outstanding cycling life with negligible capacitance fading over 1000 *** study could lead the way for the development of heteroatom-doped porous carbon nanomaterials applied to Li-based energy storage applications.

关键词： Furfural residue Ammonium persulfate Sheet-like carbon Lithium-ion capacitors Hard carbon

MOF‐derived 1D/3D N‐doped porous carbon for spatially confined electrochemical CO2 reduction to adjustable syngas

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Carbon Energy 2024年第8期6卷 1-13页

作者： Wei Zhang Hui Li Daming Feng Chenglin Wu Chenghua Sun Baohua Jia Xue Liu Tianyi Ma Key Laboratory for Green Synthesis and Preparative chemistry of Advanced Materials Institute of Clean Energy ChemistryCollege of ChemistryLiaoning UniversityShenyangLiaoningChina School of Science RMIT UniversityMelbourneVictoriaAustralia School of Pharmaceutical and Chemical Engineering Taizhou UniversityTaizhouZhejiangChina department of chemistry and Biotechnology Swinburne University of TechnologyHawthornVictoriaAustralia

Electrochemical reduction of CO_(2)to syngas(CO and H_(2))offers an efficient way to mitigate carbon emissions and store intermittent renewable energy in ***,the hierarchical one‐dimensional/three‐dimensional nitrogen‐doped porous carbon(1D/3D NPC)is prepared by carbonizing the composite of Zn‐MOF‐74 crystals in situ grown on a commercial melamine sponge(MS),for electrochemical CO_(2)reduction reaction(CO_(2)RR).The 1D/3D NPC exhibits a high CO/H_(2)ratio(5.06)and CO yield(31 mmol g^(−1)h^(−1))at−0.55 V,which are 13.7 times and 21.4 times those of 1D porous carbon(derived from Zn‐MOF‐74)and N‐doped carbon(carbonized by MS),*** is attributed to the unique spatial environment of 1D/3D NPC,which increases the adsorption capacity of CO_(2)and promotes electron transfer from the 3D N‐doped carbon framework to 1D carbon,improving the reaction kinetics of CO_(2)*** results and charge density difference plots indicate that the active site of CO_(2)RR is the positively charged carbon atom adjacent to graphitic N on 1D carbon and the active site of HER is the pyridinic N on 1D *** presence of pyridinic N and pyrrolic N reduces the number of electron transfer,decreasing the reaction kinetics and the activity of CO_(2)*** CO/H_(2)ratio is related to the distribution of N species and the specific surface area,which are determined by the degree of spatial confinement *** CO/H_(2)ratios can be regulated by adjusting the carbonization temperature to adjust the degree of spatial confinement *** the low cost of feedstock and easy strategy,1D/3D NPC catalysts have great potential for industrial application.

关键词： electrochemical CO_(2)reduction reaction melamine sponge metal‐organic frameworks porous carbon syngas

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

Sustainable electrosynthesis: Enantioselective electrochemical Rh(Ⅲ)/chiral carboxylic acid-catalyzed oxidative C–H cyclization coupled with hydrogen evolution reaction

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Chinese Chemical Letters 2024年第9期35卷 1-3页

作者： Xinghui Yao Zhouyu Wang Da-Gang Yu department of chemistry Xihua UniversityChengdu 610039China Key Laboratory of Green chemistry&Technology of Ministry of Education College of ChemistrySichuan UniversityChengdu 610064China

Chiral compounds play a crucial role in the development of pharmaceuticals,pesticides,fragrances,and materials due to their unique stereochemical *** catalysis,which employs chiral catalysts to favor the production of one enantiomer over its mirror image,has emerged as a pivotal technique in the synthesis of chiral compounds[1].However,traditional asymmetric methods sometimes rely on environmentally harmful reducing or oxidizing agents,presenting a considerable challenge in the pursuit of green chemistry.

关键词： chiral oxidative catalyzed

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