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chiral ligand-protected gold nanoclusters: Considering the optical activity from a viewpoint of ligand dissymmetric field

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Progress in Natural Science:Materials International 2016年第5期26卷 428-439页

作者： Hiroshi Yao Graduate School of Material Science University of Hyogo

chirality is a geometric property of a physical, chemical, or biological object, which is not superimposable on its mirror image. Its significant presence has led to a strong demand in the development of chiral drugs, sensors,catalysts, and photofunctional materials. In recent years, chirality of nanoscale organic/inorganic hybrids has received tremendous attention owing to potential applications in chiral nanotechnology. In particular, with the recent progress in the syntheses and characterizations of atomically precise gold nanoclusters protected by achiral thiolates, atomic level origins of their chirality have been unveiled. On the other hand, chirality or optical activity in metal nanoclusters can also be introduced via the surface chiral ligands, which should be universal for the nanosystems. This tutorial review presents some optically-active metal(gold) nanoclusters protected by chiral thiolates or phosphines, and their chiroptical(or circular dichroism; CD) properties are discussed mostly from a viewpoint of the ligand dissymmetric field scheme. The examples are the gold nanoclusters protected by(R)-/(S)-2-phenylpropane-1-thiol,(R)-/(S)-mercaptosuccinic acid, phenylboronateD/L-fructose complexes, phosphine sulfonate-ephedrinium ion pairs, or glutathione. Some methodologies for versatile asymmetric transformation and chiroptical controls of the nanocluster compounds are also described.In the dissymmetric field model as the origin of optical activity, the chiroptical responses of the gold nanoclusters are strongly associated with coupled oscillator and/or CD stealing mechanisms based on the concept of induced CD(ICD) derived from a perturbation theory, so on this basis, some characteristic features of the observed CD responses of chiral ligand-protected gold nanoclusters are presented in detail. We believe that various kinds of origins of chirality found in ligand-protected gold nanoclusters may provide models for understanding those of many related nanomaterials.

关键词： chiral ligand Monolayer-protected gold nanoclusters Dissymmetric field model Induced CD Asymmetric transformation Alloying effect

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ligand Acceleration in chiral Lewis Acid Catalysis

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CCS Chemistry 2023年第12期5卷 2717-2735页

作者： Shunxi Dong Weidi Cao Maoping Pu Xiaohua Liu Xiaoming Feng Key Laboratory of Green Chemistry&Technology Ministry of EducationCollege of ChemistrySichuan UniversityChengdu 610064Sichuan

ligand-accelerated catalysis(LAC),a term originally coined by Sharpless,has been a pivotal guiding principle in the advancement of asymmetric catalysis.The discovery and understanding of LAC have not only energized the enhancement of established catalytic asymmetric transformations but also ignited the creation of novel ones.In this review,we have curated a selection of illustrative examples,delving into the profound influence that chiral ligands exert on the acceleration of Lewis acid-promoted reactions,encompassing both thermally induced and photochemical processes.The impact of a chiral ligand on various facets,including solubility,aggregation state,geometry,Lewis acidity,and photophysical properties of metal salts,has been identified as crucial determinants.Moreover,the covalent and noncovalent interactions between ligands and substrates,the creation of chiral pockets by chiral ligands and metals,as well as the alterations in the physical and chemical properties of substrates induced by Lewis acid coordination,also play significant roles.Notably,the utilization of ligandaccelerated asymmetric Lewis acid catalysis in photoreactions presents an efficient approach for addressing the challenges associated with stereocontrol.We anticipate that this review will inspire researchers to pay more attention to the role of ligands and aid in the development of new efficient ligands and asymmetric reactions.

关键词： asymmetric catalysis chiral ligand Lewis acid ligand acceleration photocatalysis

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Novel chiral Aminophosphine ligand: Synthesis and Application in Asymmetric Catalytic Hydrogenation Reaction

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Chinese Journal of Chemistry 2003年第1期21卷 66-70页

作者：陈亿新李月明林剑虹陈新滋 Department of Chemistry Guangzhou University Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery & Synthesis Department of Applied Biology and Chemical Technology The Hong Kong Polytechnic University

A new chiral aminophosphine ligand 6,6′-dimethoxy-2,2′-bis(di~phenyl~phosphinoamino)biphenyl (DMBDPPABP) was prepared and its rhodium complex was found to be an effective catalyst for the asymmetric hydrogenation of amidoacrylic acid and its derivatives. The effects of solvent and reaction temperature on enantioselectivity were also studied.

关键词： aminophosphine chiral ligand 6,6′-dimethoxy-2,2′- bis(diphenylphosphinoamino)biphenyl asymmetric hydrogenation

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New chiral ligand N-Toluenesulfonyl-2,2′-dimethoxy-6,6′-diaminobiphenyl for Catalytic Asymmetric Transfer Hydrogenation of Ketones

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Chinese Journal of Chemistry 2002年第6期20卷 606-609页

作者：陈亿新李月明林剑虹陈新滋 Department of Chemistry Guangzhou University Guangzhou Guangdong 510405 China Open Laboratory of Chirotechnology and Department of Applied Biology and Chemical Technology the Hong Kong Polytechnic University Kowloon Hong Kong China

A new chiral ligand N p toluenesulfonyl 2,2′ dimethoxy 6,6′ diaminobiphenyl (Ts DMBDPPA) was prepared from 2,2′ dimethoxy 6,6′ diaminobiphenyl via N tosylation. Its Ru(II) complex was effective catalysts for catalytic asymmetric transfer hydrogenation of aromatic ketones (with ee 's up to 69.3%).

关键词： N p toluenesulfonyl 2,2′ dimethoxy 6,6′ diaminobiphenyl chiral ligand catalytic asymmetric transfer hydrogenation

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Design and synthesis of novel 1,3-diene bridged chiral atropoisomeric diphosphine ligands for asymmetric hydrogenation ofα-dehydro amino ketones

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Science China Chemistry 2023年第10期66卷 2847-2851页

作者： Xuefeng Tan Shuang Gao Chunyan Yang Qiwei Lang Xiaobing Ding Gen-Qiang Chen Xumu Zhang Laboratory of Small Molecule Drug Discovery and Synthesis Department of ChemistrySouthern University of Science and TechnologyShenzhen 518055China Academy for Advanced Interdisciplinary Studies Southern University of Science and TechnologyShenzhen 518000China Department of Chemistry City University of Hong KongHong Kong 999077China

A series of novel atropisomeric diphosphine ligands termed Tan Phos were designed and synthesized,which has a smaller bite angle compared with that of other ligands such as BINAP.Tan Phos showed high reactivity and enantioselectivity in the rhodiumcatalyzed asymmetric hydrogenation ofα-dehydro amino ketones,and up 99%yield and 99%ee were obtained for a wide range of chiralα-amino ketones.

关键词： diphosphine asymmetric hydrogenation chiral ligand

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A New Phosphine-Amine-Oxazoline ligand for Ru-Catalyzed Asymmetric Hydrogenation of N-Phosphinylimines

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Chinese Journal of Chemistry 2018年第12期36卷 1151-1155页

作者： Xiaochen Ma Lin Qiao Guixia Liu Zheng Huang State Key laboratory of Organometallic Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of Sciences345 Lingling RdShanghai 200032China

A series of chiral phosphine‐amine‐oxazoline (PAO) ligands with an NH moiety were synthesized and applied to the ruthenium‐catalyzed asymmetric hydrogenation of N ‐phosphinylimines. The ligand bearing phenyl groups at the phosphorus moiety and isopropyl at the oxazoline moiety exhibits good activity and excellent enantioselectivity (up to 99% ee ). This catalytic system provides an efficient and mild approach to access enantioriched amines.

关键词： amines chiral ligand hydrogenation imines ruthenium

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Asymmetric Hydroformylation of Olefins Catalyzed by a chiral Diphosphite-Rhodium Complex

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Chinese Journal of Chemistry 2004年第2期22卷 203-206页

作者：鄢明黎星术陈新滋 Department of Chemistry and Chemical Engineering Suzhou University Suzhou Jiangsu 215006 China Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery & Synthesis Department of Applied Biology and Chemical Technology The Hong Kong Polytechnic University Hong Kong China

A C2-symmetrical aryl diphosphite derived from chiral binaphthol was prepared and its rhodium complex was used as catalysts in the asymmetric hydroformylation of olefins. High catalytic activity and good regioselectivity were observed. Up to 31.2% ee and 38.1% ee were achieved for the hydroformylation of 4-fluoro-styrene and vinyl acetate respectively. The influences of ligand-to-metal ratio, reaction temperature and the pressure of syn-gas on the enantioselectivity and regioselectivity were also studied.

关键词： diphosphite chiral ligand asymmetric hydroformylation olefin rhodium complex

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Sn-Mediated Catalytic Asymmetric Reduction of Carbonyl Groups by Sodium Borohydride(or Sodium Borodeuteride)

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Chinese Journal of Chemistry 2003年第7期21卷 819-823页

作者：赵刚胡建兵 State Key Laboratory of Organometallic Chemistry Laboratory of Modern Synthetic Organic ChemistryShanghai Institute of Organic ChemistryChinese Academy of Sciences Shanghai 200032 China

Two remarkable reducing agents NaBH4 (or NaBD4)/SnCl2(or SnCl4·2Et2O) with chiral ligands are applied to the asymmetric reduction of carbonyl compounds with excellent chemical yields and enantioselective excesses.

关键词： asymmetric reduction chiral ligand carbonyl com-pound

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A new class of chiral pyrrolidine ligands for homogeneous catalytic enantioselective cyclopropanation of styrene

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Chinese Journal of Chemistry 2000年第3期18卷 407-410页

作者：施敏蒋建康 Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China

A new class of chiral pyrrolidine ligands have been successfully synthesized and their chiral induction abilities have been examined in the homogeneous catalytic enantioselective cyclopropanation of styrene. 15–30% e... 详细信息

关键词： chiral ligand pyrrolidine enantioselective cyclopropanation catalyst

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Synthesis and Characterization of Two chiral Cadmium Coordination Compounds Constructed from (1S,1′S)-1,1′-(4-amino-4H-1,2,4-triazole-3,5-diyl)diethanol

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Chinese Journal of Structural Chemistry 2012年第8期31卷 1152-1158页

作者：刘训高沈丽惠洪恬顾志国沈良 College of Material Chemistry and Chemical Engineering Hangzhou Normal University State Key Laboratory of Coordination Chemistry Coordination Chemistry InstituteSchool of Chemistry and Chemical EngineeringNanjing University School of Chemical and Material Engineering Jiangnan University

Two chiral cadmium coordination compounds,（S）-[Cd（deoatrz）2 Cl2]（1）and（S）[Cd（deoatrz）2 （NO3）2]（2）（deoatrz=（1S,1 S）-1,1-（4-amino-4H-1,2,4-triazole-3,5-diyl）diethanol）,are reported.Both 1 and 2 are mononuclear,crystallizing in tetragonal P41212 chiral space group with Z=2.For1,a=11.520（3）,b=11.520（3）,c=15.175（1）,V=2013.6（1）3,Mr=527.7,Dc =1.741 g/cm 3,μ=1.386mm-1,F（000）=1064,the final GOF=1.05,R=0.0147 and wR=0.0433 for1932 observed reflections with I〉2σ（I）.For 2,a=12.201（3）,b=12.201（3）,c=15.027（4）,V=2237.1（1）3,Mr=580.8,Dc=1.725 g/cm 3,μ=1.047mm-1,F（000）=1176,the final GOF=1.00,R=0.0201 and wR=0.0415 for 2408 observed reflections with I〉2σ（I）.Compounds 1 and 2 are connected into three-dimensional supramolecular networks through hydrogen bonding interactions.

关键词： chiral ligand cadmium crystal structure hydrogen bond

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