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Operationally Simple Enantioselective Silane Reduction of Ketones by the [Ir(OMe)(cod)]₂/Azolium Catalytic System

International Journal of Organic Chemistry 2024年第1期14卷 1-19页

作者： Satoshi Sakaguchi Chika Nagao Ryo Ichihara Shogo Matsuo Department of Chemistry and Materials Engineering Faculty of Chemistry Materials and Bioengineering Kansai University Suita Japan

An operationally simple protocol was designed for the enantioselective silane reduction (ESR) of ketones using air- and moisture-stable [Ir(OMe)(cod)]2 (cod = 1,5-cyclooctadiene) (3) as a metal catalyst precursor. This reaction was driven by chiral hydroxyamide-functionalized azolium salt 2. The catalytic ESR reaction could be performed under benchtop conditions at room temperature. Treatment of 2 with 3 in THF yielded the monodentate IrCl(NHC)(cod) (NHC = N-heterocyclic carbene) complex 4 in 93% yield, herein the anionic methoxy ligand of 3 serves as an internal base that deprotonates the azolium ring of 2. The well-defined Ir complex 4 catalyzed the ESR reaction of propiophenone (6) with (EtO)2MeSiH using the pre-mixing reaction procedure. Based on this success, the catalytic ESR reaction was designed and implemented using an in situ-generated NHC/Ir catalyst derived from 2 and 3. Thus, a wide variety of aryl ketones could be reduced to the corresponding optically active alcohols in moderate to excellent stereoselectivities at room temperature without temperature control. Since the high catalytic activity of 3 was observed, we next evaluated several other transition metal catalyst precursors for the catalytic ESR reaction under the influence of 2. This evaluation revealed that Ir(acac)(cod) (acac = acetylacetonate) (28) and [IrCl(cod)]2 (5) can be successfully used as metal catalyst precursors in the ESR reaction.

关键词： Asymmetric Catalysis Enantioselective Reduction hydrosilylation reaction N-Heterocyclic Carbene Iridium

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Partially charged single-atom Ru supported on ZrO_(2) nanocrystals for highly efficient ethylene hydrosilylation with triethoxysilane

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Nano Research 2022年第7期15卷 5857-5864页

作者： Mingyan Li Shu Zhao Jing Li Xiao Chen Yongjun Ji Haijun Yu Dingrong Bai Guangwen Xu Ziyi Zhong Fabing Su Key Laboratory of Resources Chemicals and Materials(Shenyang University of Chemical Technology) Ministry of EducationShenyang 110142China State Key Laboratory of Multiphase Complex Systems Institute of Process EngineeringChinese Academy of SciencesBeijing 100190China Faculty of Materials and Manufacturing Institute of Advanced Battery Materials and DevicesBeijing University of TechnologyBeijing 100124China Department of Chemical Engineering Beijing Key Laboratory of Green Chemical Reaction Engineering and TechnologyTsinghua UniversityBeijing 100084China School of Light Industry Beijing Technology and Business UniversityBeijing 100048China Institute of Industrial Chemistry and Energy Technology Shenyang University of Chemical TechnologyShenyang 110142China Department of Chemical Engineering Guangdong Technion-Israel Institute of Technology(GTIIT)Shantou 515063China Technion-Israel Institute of Technology(IIT) Haifa 32000Israel

Homogeneous noble metal catalysts used in alkene hydrosilylation reactions to manufacture organosilicon compounds commercially often suffer from difficulties in catalyst recovering and recycling,undesired disproportionation reactions,and energyintensive purification of ***,we report a heterogeneous 0.5Ruδ+/ZrO_(2) catalyst with partially charged single-atom Ru(0.5 wt.%Ru)supported on commercial ZrO_(2) nanocrystals synthesized by the simple impregnation method followed by H2 *** used in the ethylene hydrosilylation with triethoxysilane to produce the desired ethyltriethoxysilane,0.5Ruδ+/ZrO_(2) showed excellent catalytic performance with the maximum Ru atom utilization and good recyclability,even superior to homogeneous catalyst(RuCl3·H2O).Structural characterizations and density functional theory calculations reveal the atomic dispersion of the active Ru species and their unique electronic properties distinct from the homogeneous *** reaction route over this catalyst is supposed to follow the typical Chalk-Harrod *** highly efficient and supported singleatom Ru catalyst has the potential to replace the current homogeneous catalyst for a greener hydrosilylation industry.

关键词： single-atom Ru heterogeneous catalysts hydrosilylation reaction high performance

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SILICON-CONTAINING POLY(p-ARYLENE VINYLENE)S:SYNTHESIS AND PHOTOPHYSICS

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Chinese Journal of Polymer Science 2012年第4期30卷 589-594页

作者：李书宏徐彩虹 Department of Chemistry School of ScienceBeijing Technology and Business University Institute of Chemistry Chinese Academy of Sciences

A series of new silicon-containing poly（p-arylene vinylene）s （PAVs） with anthracene units in the main chain were synthesized by hydrosilylation reaction. The introduction of organosilicon units improved the solubility of the polymers, and the π-π conjugation of polymeric chains was interrupted. These polymers behaved as blue-green light emitters with their fluorescence maximum at 447-499 nm and quantum yields in the range of 0.28-0.30 in solution.

关键词： Poly(p-arylene vinylene)s (PAVs) hydrosilylation reaction Photophysics.

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Preparation and Property of Acrylic Acid Rare Earth Complex and Its hydrosilylation

Preparation and Property of Acrylic Acid Rare Earth Complex ...

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2004 International Conference on Rare Earth Ceramics and Glass

作者：张明陈海燕陈晓松代少俊井上真一冈本弘 College of Chemistry and Chemical Engineering Yangzhou UniversityYangzhou 225002China Yangzhou College of Industrial Technology Yangzhou 225007China Changzhou Institute of Engineering Technology Changzhou 213004China College of Materials Science and Engineering Nanjing University of TechnologyNanjing 210009China Department of Material Engineering Yancheng Institute of TechnologyYancheng 224003China Department of Applied Chemistry Aichi Institute of TechnologyToyota 470-0392Japan Department of Applied Chemistry Aichi Institute of TechnologyToyota 470-0392Japan

＜正＞ Acrylic acid rare earth complex was prepared. Its chemical composition was determined by chemical and elemental analysis, and its structure as well as properties was characterized using IR, Fluorescence and UV spectrum, and its solubility was also investigated. Meanwhile a kind of elastic functional polymer with rare earth units in the side chains was produced. It is confirmed by IR spectrum that the Si - H bonds really react with acrylic acid rare earth.

关键词： acrylic acid rare earth complex polyhydromethylsiloxane hydrosilylation reaction physical property

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