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cooperative catalysis in Asymmetric Synthesis and CO2 Transformation: Case Study of Catalyst Design and Process Innovation

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Cooperative Catalysis in Asymmetric Synthesis and CO2 Transf...

中国化学会第29届学术年会

作者： Ding Kuiling State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of Sciences

The concept of "cooperative catalysis" has been recognized as one of the most powerful approaches for stimulating innovations to revolutionize the processes of pharmaceutical, material and chemical industries.[1] In this talk, several case studies in our lab on the design of highly efficient molecular catalysts and the development of new sustainable processes on the basis of "cooperative catalysis" will be presented, including an integrated Salen/M catalyst for asymmetric cyanation of aldehydes,[2] a bifunctional SKP/Pd catalyst for asymmetric allylic amination of MBH adducts,[3] and a new process from CO2 to methanol via a hydrogenation of ethylene carbonate under mild conditions（Scheme 1）.[4]

关键词： asymmetric catalysis cooperative catalysis titanium palladium ruthenium

cooperative catalysis in Asymmetric Synthesis:Case Studies of Mechanistic Understanding and Process Innovation

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Cooperative Catalysis in Asymmetric Synthesis:Case Studies o...

中国化学会第十三届全国有机合成化学学术研讨会

作者： Kuiling Ding State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of Sciences

The concept of "cooperative catalysis" has been recognized as one of the most powerful approaches for stimulating innovations to revolutionize the processes of pharmaceutical,material and chemical industries.[1] In this talk,several case studies in our lab on the design of highly efficient molecular catalysts and the development of new sustainable process on the basis of "cooperative catalysis" will be presented,including a chiral titanium catalyst for asymmetric ring-opening of epoxide,[2] an integrated Salen/M catalyst for asymmetric cyanation of aldehydes,[3] and a bifunctional SKP/Pd catalyst for asymmetric allylic amination of MBH adducts.[4]

关键词： asymmetric catalysis cooperative catalysis palladium SKP ligands allylic amination

cooperative catalysis in Asymmetric Synthesis and CO2 Transformation:Case Study of Catalyst Design and Process Innovation

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Cooperative Catalysis in Asymmetric Synthesis and CO2 Transf...

中国化学会全国第十一届有机合成化学学术研讨会

作者： Ding Kuiling State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of Sciences

The concept of "cooperative catalysis"has been recognized as one of the most powerful approaches for stimulating innovations to revolutionize the processes of pharmaceutical,material and chemical industries.In this talk,several case studies in our lab on the design of highly efficient molecular catalysts and the development of new sustainable processes on the basis of "cooperative catalysis" will be presented,including an integrated Salen/M catalyst for asymmetric cyanation of aldehydes,a bifunctional SKP/Pd catalyst for asymmetric allylic amination of MBH adducts,and a new process from CO to methanol via a hydrogenation of ethylene carbonate under mild conditions(Scheme 1).

关键词： Asymmetric catalysis cooperative catalysis Titanium Palladium Ruthenium

Iridium and B(C_(6)F_(5))_(3) co-catalyzed chemoselective deoxygenative reduction of tertiary amides:application to the efficient synthesis and late-stage modification of pharmaceuticals

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Science China Chemistry 2023年第4期66卷 1094-1100页

作者： Feng Han Guang-Sheng Lu Dong-Ping Wu Pei-Qiang Huang Department of Chemistry Fujian Provincial Key Laboratory of Chemical BiologyCollege of Chemistry and Chemical EngineeringXiamen UniversityXiamen 361005China

The Vaska’s complex—tris(pentafluorophenyl)borane combination was found to be a highly efficient cooperative catalysis system for the hydrosilylative reduction of tertiary amides to yield amines under mild conditions.The reaction shows high chemoselectivity,tolerating halide,phenolyl,alkenyl,nitro,nitrile,ester,azido,ketone,and enone functional groups.For unsubstituted cyclohexanone carboxamide,two variations were established to achieve either catalytic concomitant reduction of the two carbonyl groups or selective reduction of the amide carbonyl.The protocol was applied to the efficient synthesis and latestage modification of several pharmaceuticals and derivatives.Importantly,we showed that by simply prolonging reaction time to 24–28 h,the reaction can reach an exceptionally high efficiency with turnover number(TON)up to 9.8×10^(6) and turnover frequency(TOF)up to 408,333 at a quite low catalyst loading of 0.00001 mol%(S/C(Ir)=10,000,000).

关键词： amide reduction cooperative catalysis chemoselectivity hydrosilylation amines

Stereodivergently asymmetric synthesis of chiral phosphorus compounds by synergistic combination of ion-pair catalyst and base

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Science China Chemistry 2022年第12期65卷 2500-2511页

作者： Hui-Lin Hu Xiaoyu Ren Jiajia He Lixiang Zhu Siqiang Fang Zhishan Su Tianli Wang Key Laboratory of Green Chemistry&Technology Ministry of EducationCollege of ChemistrySichuan UniversityChengdu610064China

Stereodivergently constructing the designed products having adjacent multi-stereocenters via a given reaction,with excellent control of both absolute and relative configurations,presents one of the substantial hurdles in asymmetric catalysis.Herein,we report a precisely stereodivergent asymmetric protocol by synergistic combination of phosphonium-involved ion-pair catalysis and base for accessing to chiral phosphorus compounds bearing two adjacent chiral centers particularly containing an acidic protonated enantioenriched carbon atom,having broad functional group compatibility in both dynamic and thermodynamic processes under mild reaction conditions.Two keys for the success in constructing these stereoisomers with high levels of regio-,diastereo-,and enantioselectivities were contained:firstly,the precise stereo-control in providing dynamic products was enabled by bifunctional phosphonium salt catalyst with semi-enclosed cavity;secondly,the readily stereospecific transformation of adducts from dynamic to thermodynamic version was initiated by achiral base.All four stereoisomers could be readily accessed even in gram-scale in high yields with maintaining excellent stereoselectivities,illustrating the potential of this synergistic catalytic methodology in organic synthesis.Moreover,mechanistic studies including density functional theory(DFT)calculations and control experiments provide insights into the mechanism.

关键词： stereodivergent asymmetric synthesis chiral phosphorus compounds dipeptided phosphonium salts cooperative catalysis base control

Recent Progress of Asymmetric catalysis from a Chinese Perspective

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CCS Chemistry 2023年第12期5卷 2685-2716页

作者： Yan-Mei He Yuan-Zheng Cheng Yingdong Duan Yan-Dong Zhang Qing-Hua Fan Shu-Li You Sanzhong Luo Shou-Fei Zhu Xue-Feng Fu Qi-Lin Zhou Beijing National Laboratory for Molecular Sciences Institute of ChemistryChinese Academy of SciencesBeijing 100190 State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032 Center of Basic Molecular Science Department of ChemistryTsinghua UniversityBeijing 100084 State Key Laboratory and Institute of Elemento-Organic Chemistry College of ChemistryNankai UniversityTianjin 300071 Department of Chemical Sciences National Natural Science Foundation of ChinaBeijing 100085

The precise construction of chiral molecules is a core research area in chemical science and technology.Among the plethora of reported synthetic methods,asymmetric catalysis has emerged as one of the most efficient and direct ways to obtain optically pure chiral compounds.This article mainly reviews the recent progress of asymmetric catalysis made by Chinese chemists from the following aspects:the development of new chiral ligands,transition metal-catalyzed asymmetric reactions,asymmetric organocatalytic reactions,and new strategies for asymmetric catalysis.This review does not intend to be comprehensive;only representative examples are selected to highlight the important progress made in this field.Finally,a brief outlook is given on the development of novel chiral ligands/catalysts,new enantioselective reactions,and their applications in chiral drugs and agricultural chemicals.

关键词： asymmetric catalysis chiral ligands organocatalysts enantioselective reactions cooperative catalysis

Enantioselective protonation reactions via cooperative photoredox and asymmetric H-bonding catalysis

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Enantioselective protonation reactions via cooperative photo...

中国化学会·第十五届全国有机合成化学学术研讨会

作者： Yanli Yin Meimei Hou Lu Lin 江智勇 Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province Henan University 河南大学

In recent years, asymmetric H-bonding catalysis as one of the most important organocatalytic strategies has been merged with photoredox catalysis to present a new and powerful synthetic approach to access valuable but challenging molecular architectures.As an extension of our research interest in asymmetric H-bonding catalysis and photoredox catalysis, we report the use of such a cooperative catalysis platform in a series of enantioselective protonation reactions, including reductive protonation of activated ketones and imines(Fig.1a), dehalogenative protonation(Fig.1b), and conjugate addition-protonation(Fig.1c).

关键词： photoredox catalysis H-bonding catalysis cooperative catalysis asymmetric catalysis protonation

cooperative Dual Organocatalytic Asymmetric Decarboxylative[4+3]Annulations with Benzoxazinanones

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Precision Chemistry

Precision Chemistry 2023年第4期1卷 241-247页

作者： Ling Zhu Teng Xie Jin Song Liu-Zhu Gong Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry University of Science and Technology of ChinaHefei 230026China Institutes of Physical Science and Information Technology Key Laboratory of Environment-Friendly Polymeric Materials of Anhui ProvinceAnhui UniversityHefei 230601China Center for Excellence in Molecular Synthesis of Chinese Academy of Sciences Hefei 230026China

The cooperative catalysis of an achiral Lewis base and a chiral N-heterocyclic carbene(NHC)enables a highly enantioselective[4+3]annulation of benzoxazinanones with isatin-derived enals.DMAP serves as a nucleophilic Lewis base to promote decarboxylation of benzoxazinanones,which leads to azaortho-xylylene intermediates that undergo[4+3]annulations with NHC-bound homoenolates.This method breaks the substrate scope limitation of transition-metal-catalyzed variants,thus a broader range of benzoxazinanones are tolerated,and provides a straightforward entry to enantioenriched spirooxindoles in high structural diversity.

关键词： cooperative catalysis chiral N-heterocyclic carbene [4+3]annulation benzoxazinanones spirobenzazepinone

Predictable site-selective radical fluorination of tertiary ethers

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Science China Chemistry 2020年第2期63卷 187-191页

作者： Junyang Ma Wentao Xu Jin Xie State Key Laboratory of Coordination Chemistry Jiangsu Key Laboratory of Advanced Organic MaterialsChemistry and Biomedicine Innovation CenterSchool of Chemistry and Chemical EngineeringNanjing University

In this communication,we disclose the first example of metal-free and site-selective radical fluorination of readily available tertiary alkyl ethers,enabled by synergistic photocatalysis and organocatalysis.This catalytic combination allows for exclusive fluorination of tertiary C–O bonds under mild conditions even in the presence of competing reaction sites.The excellent functional group tolerance affords valuable access to sterically hindered alkyl fluorides through late-stage modification of complex molecules.The successful use of tertiary alkyl ethers in radical fluorination enhances the structural diversity of aliphatic fluorides that can be derived from naturally abundant alcohols.

关键词： cooperative catalysis C–O bond activation radical fluorination polarity-matching effect umpolung