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Transition-metal-free coupling reactions involving gem–diborylalkanes

Chinese Chemical Letters 2023年第7期34卷 17-22页

作者： Yongli Li Dalong Shen Hao Zhang Zhenxing Liu College of Chemistry Zhengzhou UniversityZhengzhou 450002China

Due to the increasing demand for the sustainability of modern organic chemistry, the development of green and powerful methods for C-C and C-B bond formation is highly desired. Among them, the transition-metal-free coupling reactions of gem–diborylalkanes emerge as one valuable tool for organic chemists in the last decade. The review covers selected representative examples. A comparison of these reactions with transition-metal-catalyzed reactions is provided. The recent example of α-boryl radical formation from gem–diborylalkanes is also briefly discussed.

关键词： Transition-metal-free coupling reactions gem–Diborylalkane Sustainable chemistry Radical

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Porous polymer supported palladium catalyst for cross coupling reactions with high activity and recyclability

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Science China Chemistry 2012年第4期55卷 2095-2103页

作者： SUN Qi ZHU LongFeng SUN ZhenHua MENG XiangJu XIAO Feng-Shou Key Lab of Applied Chemistry of Zhejiang Provinee Department of ChemistryZhejiang University(XiXi Campus)Hangzhou 310028China State Key Laboratory of Inorganic Synthesis and Preparative Chemistry Jilin University Changchun 130012China Shenyang National Laboratory for Materials Science Institute of Metal ResearchChinese Academy of SciencesShenyang 110016China

Porous polymer supported palladium catalyst for cross coupling reactions with high activity has been successfully prepared by coordination of Pd 2+ species with Schiff bases functionalized porous polymer. The catalyst has been systemically investi-gated by a series of characterizations such as TEM, N 2 adsorption, NMR, IR, XPS, etc. TEM and N 2 isotherms show that the sample maintains the nanoporous structure after the modification and coordination. XPS results show that chemical state of palladium species in the catalyst is mainly +2. More importantly, the catalyst shows very high activities and excellent recycla-bility in a series of coupling reactions including Suzuki, Sonogashira, and Heck reactions. Hot filtration and poison of catalysts experiments have also been performed and the results indicate that soluble active species (mainly Pd(0) species) in-situ gener-ated from the catalyst under the reaction conditions are the active intermediates, which would redeposit to the supporter after the reactions.

关键词： heterogenous catalysis Pd coupling reactions nanoporous polymers

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Conjugated Porous Networks Based on Cyclotriveratrylene Building Block for Hydrogen Adsorption

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Chinese Journal of Chemistry 2013年第5期31卷 617-623页

作者： Xiaona Han Lei Li Zhitang Huang Junmin Liu Qiyu Zheng Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Molecular Recognition and Function Institute of Chemistry Chinese Academy of Sciences Beijing 100190 China School of Chemistry and Chemical Engineering Institute of Physical Chemistry Sun Yat-Sen University Guangzhou Guangdong 510275 China

Macrocyclic CTV-Br3 reacted with the linear benzene-1,4-diboronic acid and 1,4-diethynylbenzene via Suzuki and Sonogashira-Hagihara coupling reactions producing the rigid porous materials CTV-CMP-1 and CTV-CMP-2. The porous materials have good thermal and chemical stability. The Brunauer-Emmet-Teller specific surface areas of CTV-CMP-1 and CTV-CMP-2 are 314 and 218 cm2·g^-1, respectively. Physical properties of the porous materi- als were investigated, CTV-CMP-1 showed moderate hydrogen adsorption about 0.81 wt% at 1.13 bar while CTV-CMP-2 showed lower hydrogen adsorption about 0.51 wt%. These materials are analogs to activated carbons which could be potentially used in gas separation and organic compound adsorption.

关键词： cyclotriveratrylene coupling reactions conjugated microporous polymers hydrogen adsorption

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Recent Advances of Modern Protocol for C-C Bonds—The Suzuki Cross-coupling

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Advances in Chemical Engineering and Science 2013年第3期3卷 19-32页

作者： Jadwiga Soloducho Kamila Olech Agnieszka Swist Dorota Zajac Joanna Cabaj Faculty of Chemistry Wroclaw University of TechnologyWroclawPoland

Over the past 20 years, small molecule solid phase synthesis has become a powerful tool in the discovery of novel molecular materials. In the development of organic chemistry, the carbon-carbon bond formation has always been one of the most useful and fundamental reaction. The current review summarizes recent developments in metal-catalyzed coupling reactions. The following method is discussed in detail—the cross-coupling of aryl halides with aryl boronic acids (the Suzuki coupling), and the others C-C bond formation reactions as the palladium-catalyzed reaction between an aryl and (or) alkyl halide and a vinyl functionality (the Heck reaction);and the palladium-catalyzed cross-coupling reaction of organostannyl reagents with a variety of organic electrophiles (the Stille reaction)—are mentioned.

关键词： C-C Bond Formation coupling reactions Palladium Catalysts Suzuki coupling Heterocyclic Copolymers

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SYNTHESIS OF FUNCTIONAL MACROMOLECULE INTERMEDIATE THROUGH coupling REACTION CATALYZED BY [bmim]Cl/FeCl_3 IONIC LIQUID

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Chinese Journal of Reactive Polymers 2006年第2期15卷 108-114页

作者： CHEN Min CHEN Xiaonong YUAN Xinhua ZHANG Yan ZHANG Chunyan LIU Hua DAI Qixun College of Chemical Engineering Jiangsu UniversityZhenjiang 212013China College of Material Science and Engineering Jiangsu UniversityZhenjiang212013China

To obtain new functional aromatic polymer materiul. 3,3＇-biacenaphthene, which is used as macromolecule intermediate of,funcrion aromatic polymer material, was synthesized through the coupling reaction of acenaphthene catalyzing by ionic liquid （[bmim]CI/FeCl3） at mild reaction condition. Pure 3,3＇-biacenaphthene was obtained hy recrystalling and column chromatography from the reaction mixture and was determined by GC/MS, SHNMR arid FTIR analysis. The influence of various reaction conditions on the yield of 3,3＇-biacenaphthene were studied by GC analysis. The result shows that the optimun synthesis conditions of the coupling reaction are, as following： the molar ratio of FeCl3 to [BmimlCl being 3, the mole ratio of FeCl3 in [Bmim]Cl/FeCl3 to acenaphthene being 4. the reaction temperamre being 20 ℃ the reaction time being 4h and the solvent of the reaction system being PhNO2 Under those conditions, the yield of the 3.3＇-biacenaphthene will be 48.71% and selectivity, of that will be 78.56 %. Farther more, [bmim]Cl/FeCl3 has no pollution to environments and can be reused.

关键词： Functional macromolecule, intermediate 3,3'-biacenaphthene Synthesis coupling reactions Ionic liquid Catalyze

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Metal-direct on-surface synthesis

Metal-direct on-surface synthesis

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中国化学会第30届学术年会

作者： Nian Lin Department of Physics The Hong Kong University of Science and Technology

We report on our recent studies of on-surface coupling reactions and focus on the roles of the transition metals in the reaction. First, we examine the catalytic efficiency of Cu, Au, Ag, Pt, and Pd in Ullmann coupling. We analyze the bond formation yields when the reaction takes place in the presence of these metals and we determine the rate constants and activation energy of Cu- and Pd-catalyzed reaction. In the second part, we demonstrate a strategy of using metal coordination template to steer the on-surface polymerization reactions toward specific products. In the third part, we show that a cross-coupling reaction, the Sonogashira coupling, can be achieved on a Au（111） surface aided by metal-organic template.

关键词： on-surface coupling reactions

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