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Recent advances in gold-complex and chiral organocatalyst cooperative catalysis for asymmetric alkyne functionalization

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Chinese Chemical Letters 2022年第12期33卷 4969-4979页

作者： Ming Bao Su Zhou Wenhao Hu Xinfang Xu Guangdong Key Laboratory of Chiral Molecule and Drug Discovery School of Pharmaceutical SciencesSun Yat-sen UniversityGuangzhou 510006China

Homogeneous gold catalysis has demonstrated the preponderant capability of realizing a broad range of synthetically versatile alkyne functionalization over the last two *** catalytic asymmetric alkyne transformation has focused on the principle of using gold catalysts either associated with chiral phosphine ligand or combined with chiral counterion,a variety of breakthroughs have been reported with the application of gold-complex and chiral organocatalyst cooperative catalysis strategy,which could enable the challenging transformations that cannot be realized by mono-catalysis with excellent *** review will cover two general protocols in this field,including relay catalysis and synergistic catalysis,with emphasis on the detailed cooperative catalysts models to illustrate the roles of the two catalysts and highlight the potential synthetic opportunities offered by asymmetric cooperative catalysis.

关键词： gold catalysis Chiral organocatalyst catalysis Relay catalysis Synergistic catalysis Asymmetric alkyne functionalization

Anisotropic gold nanoparticles: Preparation and applications in catalysis

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Chinese Journal of catalysis 2016年第10期37卷 1619-1650页

作者： Peter Priecel Hammed Adekunle Salami Romen Herrera Padilla Ziyi Zhong Jose Antonio Lopez-Sanchez 利物浦大学化学系可再生能源斯蒂芬森研究所英国利物浦新加坡科技研究局(A*STAR) 化学与工程科学研究所新加坡裕廊岛627833

Despite the high amount of scientific work dedicated to the gold nanoparticles in catalysis, most of the research has been performed utilising supported nanoparticles obtained by traditional impreg‐nation of gold salts onto a support, co‐precipitation or deposition‐precipitation methods which do not benefit from the recent advances in nanotechnologies. Only more recently, gold catalyst scien‐tists have been exploiting the potential of preforming the metal nanoparticles in a colloidal suspen‐sion before immobilisation with great results in terms of catalytic activity and the morphology con‐trol of mono‐and bimetallic catalysts. On the other hand, the last decade has seen the emergence of more advanced control in gold metal nanoparticle synthesis, resulting in a variety of anisotropic gold nanoparticles with easily accessible new morphologies that offer control over the coordination of surface atoms and the optical properties of the nanoparticles （tunable plasmon band） with im‐mense relevance for catalysis. Such morphologies include nanorods, nanostars, nanoflowers, den‐dritic nanostructures or polyhedral nanoparticles to mention a few. In addition to highlighting newly developed methods and properties of anisotropic gold nanoparticles, in this review we ex‐amine the emerging literature that clearly indicates the often superior catalytic performance and amazing potential of these nanoparticles to transform the field of heterogeneous catalysis by gold by offering potentially higher catalytic performance, control over exposed active sites, robustness and tunability for thermal‐, electro‐and photocatalysis.

关键词： Anisotropic metal nanoparticles gold nanoparticles gold catalysis Photocatalysis Electrocatalysis Catalytic oxidation Colloidal gold nanoparticles gold nanorod gold nanostars Sol immobilisation

gold-catalyzed ketene dual functionalization and mechanistic insights:divergent synthesis of indenes and benzo[d]oxepines

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Science China Chemistry 2021年第5期64卷 778-787页

作者： Ming Bao Jinzhou Chen Chao Pei Sujie Zhang Jinping Lei Wenhao Hu Xinfang Xu Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery School of Pharmaceutical SciencesSun Yat-sen UniversityGuangzhou 510006China

An unprecedented gold-catalyzed ketene C=O/C=C bifunctionalization method has been *** studies and density function theory(DFT)calculations indicate that the reaction is initiated by gold-catalyzed Wolff rearrangement of diazoketone to form the ketene intermediate,followed by intermolecular nucleophilic addition and terminated with two divergent cyclization processes via enol *** the case with alcohols as the nucleophiles,the reaction goes through a C-5-endodig carbocyclization to give the indene products;whereas,O-7-endo-dig cyclization occurs dominantly when indoles/pyrroles are used as the nucleophiles,delivering the 7-membered benzo[d]*** comparison with the well-documented cycloaddition and nucleophilic addition reactions,this cascade reaction features a novel reaction pattern for the ketene dual functionalization through addition with nucleophile and electrophile in sequence.

关键词： metal carbene ketene dual functionalization Wolff rearrangement gold catalysis indene benzo[d]oxepine

Morphology-selective synthesis of active and durable gold catalysts with high catalytic performance in the reduction of 4-nitrophenol

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Nano Research 2016年第10期9卷 3099-3115页

作者： Daowei Gao Xin Zhang Xiaoping Dai Yuchen Qin Aijun Duan Yanbing Yu Hongying Zhuo Hairui Zhao Pengfang Zhang Yan Jiang Jianmei Li Zhen Zhao State Key Laboratory of Heavy Oil Processing China University of Petroleum Beijing 102249 China College of Science China University of Petroleum Beijing 102249 China

A series of novel catalysts consisting of nanosized Au particles confined in micro-mesoporous ZSM-5/SBA-15 （ZSBA） materials with platelet （PL）, rod （RD）, and hexagonal-prism （HP） morphologies have been synthesized in situ. These catalysts possess both SBA-15 and ZSM-5 structures and exhibit excellent stability of their active sites by confinement of the Au nanoparticles （NPs） within ZSBA. The catalysts have been characterized in depth to understand their structure-property relationships. The gold NP dimensions and the pore structure of the catalysts, which were found to be sensitive to calcination temperature and synthetic conditions, are shown to play vital roles in the reduction of 4-nitrophenol. Au/ZSBA-PL, with short mesochannels （210 nm） and a large pore diameter （6.7 nm）, exhibits high catalytic performance in the reduction of 4-nitrophenol, whereas Au/ZSBA-HP and Au/ZSBA-RD, with long mesochannels and relatively smaller pore sizes, show poor catalytic activities. In the case of catalysts with different gold NP sizes, Au/ZSBA-PL-350 with an Au NP diameter of 4.0 nm exhibits the highest reaction rate constant （0.14 min-1） and turnover frequency （0.0341 s-1）. In addition, the effect of the reaction parameters on the reduction of 4-nitrophenol has been systematically investigated. A possible mechanism for 4-nitrophenol reduction over the Au/ZSBA catalysts is proposed.

关键词： gold catalysis porous material environmental pollution 4-nitrophenol

Theoretical investigation of gold based model catalysts

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Science China Chemistry 2015年第4期58卷 565-573页

作者： Wenhua Zhang Weixin Huang Jinlong Yang Key Lab of Materials for Energy Conversion Department of Materials Science and Engineering University of Science and Technology of China Synergetic Innovation Center of Quantum Information & Quantum Physics University of Science and Technology of China Hefei National Lab for Physical Sciences at the Microscale

With potential applications in various fields, gold related catalysts have received intensive attentions. In the past decade, mechanisms of gold catalysis for low-temperature CO oxidation, NOx oxidation/reduction, selective oxidation of alcohols have been investigated both experimentally and theoretically based on model catalysts using free or supported gold nanoparticles and single crystal gold surfaces. In this short review, we summarize recent theoretical studies on molecular oxygen activation process, water or hydroxyl involved oxidation reaction, and also the effect of local structure on the reactivity and selectivity.

关键词： gold catalysis CO oxidation mechanism NO reduction alcohol selective oxidation local structure effect

Selective and stable Au-Cu bimetallic catalyst for CO-PROX

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Nano Research 2023年第7期16卷 9031-9038页

作者： Feng Hong Guanjian Cheng Weihao Hu Shengyang Wang Qike Jiang Junhong Fu Botao Qiao Jiahui Huang Dalian National Laboratory for Clean Energy Dalian Institute of Chemical PhysicsChinese Academy of SciencesDalian 116023China College of Energy Soochow Institute for Energy and Materials Innovations(SIEMIS)Soochow UniversitySuzhou 215006China CAS Key Laboratory of Science and Technology on Applied catalysis Dalian Institute of Chemical PhysicsChinese Academy of SciencesDalian 116023China State Key Laboratory of catalysis Dalian Institute of Chemical PhysicsChinese Academy of SciencesDalian 116023China School of Chemistry and Chemical Engineering Yulin UniversityYulin 719000China University of Chinese Academy of Sciences Beijing 100049China

gold-based catalysts are promising in CO preferential oxidation(CO-PROX)reaction in H_(2)-rich stream on account of their high intrinsic activity for CO elimination even at ambient ***,the decrease of CO conversion at elevated temperature due to the competition of H_(2)oxidation,together with the low stability of gold nanoparticles,has posed a dear ***,we report that Au-Cu bimetallic catalyst prepared by galvanic replacement method shows a wide temperature window for CO total conversion(30-100℃)and very good catalyst stability without deactivation in a 200-h *** characterizations combined with density functional theory(DFT)calculation reveal that the synergistic effect of Au-Cu,the electron transfer from Au to Cu,leads to not only strengthened chemisorption of CO but also weakened dissociation of H_(2),both of which are helpful in inhibiting the competition of H_(2)oxidation thus widening the temperature window for CO total conversion.

关键词： gold catalysis CO preferential oxidation(CO-PROX) electronic interaction galvanic replacement

Dinuclear gold-catalyzed C–H bond functionalization of cyclopropenes

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Science China Chemistry 2021年第11期64卷 1958-1963页

作者： Kai Liu Tingrui Li Duan-Yang Liu Weipeng Li Jian Han Chengjian Zhu Jin Xie State Key Laboratory of Coordination Chemistry Jiangsu Key Laboratory of Advanced Organic MaterialsChemistry and Biomedicine Innovation Center(ChemBIC)School of Chemistry and Chemical EngineeringNanjing UniversityNanjing210023China College of Chemical Engineering Zhejiang University of TechnologyHangzhou310014China College of Chemistry and Molecular Engineering Zhengzhou UniversityZhengzhou450001China Advanced Catalytic Engineering Research Center of the Ministry of Education Hunan UniversityChangsha410082China

We report an unprecedented C-H bond functionalization of cyclopropenes enabled by dinuclear gold *** selective C-H allylation,alkynylation and halogenation of cyclopropenes with organic halides have been *** reaction does not require strong external oxidants and affords access to functionalized cyclopropenes in moderate to good *** reductive elimination process to controllably construct C-C or C-X bonds can be tuned by using different dinuclear gold catalysts.

关键词： cyclopropenes gold catalysis allylation alkynylation C–H activation

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An Anomeric Base-Tolerant Ester of 8-Alkynyl-1-naphthoate for gold(I)-Catalyzed Glycosylation Reaction

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Chinese Journal of Chemistry 2023年第11期41卷 1305-1312页

作者： Xiaojuan Zhang Peng Xu Zhengbing Zhou Yazhou Zhang Biao Yu Yugen Zhu Zhongshan Institute for Drug Discovery Shanghai Institute of Materia MedicaChinese Academy of SciencesZhongshanGuangdong528400 China Key Laboratory of Medicinal Chemistry for Natural Resource Ministry of EducationYunnan Provincial Center for Research&Development of Natural ProductsSchool of Chemical Science and TechnologyYunnan UniversityKunmingYunnan650091 China State Key Laboratory of Bioorganic and Natural Products Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai200032 China

Given the extreme complexity and diversity of carbohydrates,efficient approaches to the homogeneous oligosaccharide remain *** synthesis represents one of the most reliable methods to access homogeneous samples,which mainly relies on the key glycosylation *** with enormous efforts to develop leaving groups for establishing robust glycosylation protocols,we herein disclose a structurally novel leaving group of 8-phenylethynyl-1-naphthoate that is able to enable efficient glycosylation reactions under the extremely mild condition of gold(I)-***,the anomeric naphthoate possesses the unprecedent character of base-stability in sharp contrast to the conventional ester groups at anomeric position of carbohydrates,which endows high compatibility with a variety of chemical ***,the present glycosylation protocol with 8-phenylethynyl-1-naphthoate as leaving group is able to realize minimally protected glycosylation *** studies reveal a unique structure of 8-phenylethynyl-1-naphthoate that accounts for the reason for these characteristics.

关键词： Glycosylation Leaving Group gold catalysis Anomeric Ester Base Tolerant Carbohydrates

Exploration of structure sensitivity of gold nanoparticles in low-temperature CO oxidation

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Industrial Chemistry & Materials

Industrial Chemistry & Materials 2024年第2期2卷 321-327页

作者： Lei Ying Yu Han Beien Zhu Yi Gao Key Laboratory of Interfacial Physics and Technology Shanghai Institute of Applied PhysicsChinese Academy of SciencesShanghai 201800China University of Chinese Academy of Sciences Beijing 100049China Phonon Science Research Center for Carbon Dioxide Shanghai Advanced Research InstituteChinese Academy of SciencesShanghai 201210China Key Laboratory of Low-Carbon Conversion Science&Engineering Shanghai Advanced Research InstituteChinese Academy of SciencesShanghai 201210China

gold nanoparticles(NPs)exhibit remarkable catalytic activity in low-temperature CO oxidation and their performance is highly dependent on size and ***,the underlying mechanism isn't fully understood ***,we combine density functional theory calculations,a multiscale structure reconstruction model,and kinetic Monte Carlo simulations to investigate the activity and structure sensitivity of Au NPs under different reaction *** results indicate that increasing the partial pressure ratio of O_(2) to CO leads to the decrease of optimal reaction temperature accompanied with the increase of *** low temperatures,the morphology of the NPs evolves to expose a higher proportion of(110)facets to promote the activity ***,the size dependence analysis suggests that O_(2)-rich conditions are favorable for small-sized NPs,while CO-rich conditions favor the large-sized *** findings not only enrich our basic understanding of the structure–reactivity relationship and the origin of structure sensitivity in gold-catalysis,but provide a guide for rational design of Au catalysts.

关键词： Kinetic Monte Carlo CO oxidation gold catalysis Nanoparticles