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Recent applications of macrocycles in supramolecular catalysis

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Chinese Chemical Letters 2024年第4期35卷 132-141页

作者： Conghui Wang Lei Xu Zhenhua Jia Teck-peng loh College of Advanced Interdisciplinary Science and Technology Henan University of TechnologyZhengzhou 450001China Division of Chemistry and Biological Chemistry School of Chemistry Chemical Engineeringand BiotechnologyNanyang Technological UniversitySingapore 637371Singapore Institute of Advanced Synthesis School of Chemistry and Molecular Engineering Nanjing Tech UniversityNanjing 211816China

Numerous supramolecular macrocycles have been utilized for developing catalysts by exploiting their specific molecular recognition and ability to form inclusion complexes through noncovalent interactions. The cyclic structure and modified functional groups of these macrocycles can influence substrate and transition state stability, as well as reaction selectivity. The inner cavities of these macrocycles are particularly beneficial, as they enable substrates to adopt preorganized arrangements and serve as versatile platforms for highly efficient supramolecular catalytic systems. This minireview provides an overview of recent advancements in supramolecular catalysis using various macrocycles, such as crown ethers, cyclodextrins,calixarenes, pillararenes, cucurbiturils, and other novel macrocycles.

关键词： Supramolecular catalysis Macrocycle Host-guest interactions Confinement Selectivity

Strategies for constructing seven-membered rings:Applications in natural product synthesis

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Chinese Chemical Letters 2024年第6期35卷 53-70页

作者： peng Chen Lijuan Liang yufei Zhu Zhimin Xing Zhenhua Jia Teck-peng loh College of Advanced Interdisciplinary Science and Technology Henan University of TechnologyZhengzhou 450001China Division of Chemistry and Biological Chemistry School of Chemistry Chemical Engineeringand BiotechnologyNanyang Technological UniversitySingapore 637371Singapore Institute of Advanced Synthesis School of Chemistry and Molecular Engineering Nanjing Tech UniversityNanjing 211816China State Key Laboratory of Applied Organic Chemistry Department of ChemistryLanzhou UniversityLanzhou 730000China

The seven-membered ring motifs are found in bioactive pharmaceuticals and a wide range of natural products,including alkaloids and terpenoids,which hold significant importance in synthetic chemistry and has garnered considerable attention from both academia and *** the challenges faced in the past decade,the total synthesis of natural products incorporating the non-aromatic cycloheptane skeletons remains a compelling ***,numerous elegant strategies for constructing the sevenmembered ring system have been successfully *** review focuses on the recent advancements in this field from 2017 to April 2023,highlighting key transformations utilized to construct the non-aromatic cycloheptane core structures and serves as a valuable guide for synthetic chemists engaged in the total synthesis of natural products containing seven-membered ring motifs.

关键词： Seven-membered rings Total synthesis Natural products Synthetic strategy Cycloheptane

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三芳基碳正离子在有机合成中的应用

有机化学 2024年第2期44卷 421-437页

作者：李路瑶贺忠文张振国贾振华罗德平河南工业大学前沿交叉科学与技术学院郑州450001 南洋理工大学物理与数学科学学院化学与生物化学系新加坡637371

三芳基碳正离子作为一种优异的路易斯酸,其最低空分子轨道(LUMO)轨道能级较低,易接受一对电子,被广泛应用于合成转化中,是重要的试剂和催化剂.近年来,三芳基碳正离子在有机合成中主要被用作催化剂、预催化剂、共催化剂和添加剂.此外,三... 详细信息

三芳基碳正离子作为一种优异的路易斯酸,其最低空分子轨道(LUMO)轨道能级较低,易接受一对电子,被广泛应用于合成转化中,是重要的试剂和催化剂.近年来,三芳基碳正离子在有机合成中主要被用作催化剂、预催化剂、共催化剂和添加剂.此外,三芳基碳正离子作为关键中间体,可以成功应用于四芳基甲烷的合成.综述了近年来三芳基碳正离子在有机合成中的应用进展,并总结了三芳基碳正离子在有机合成中的多种功能作用,希望引起广泛的关注.

关键词：三芳基碳正离子催化剂有机合成无金属

Rhodium-Catalyzed Defluorinative Vinylation of gem-Difluoroalkenes for the Synthesis of 2-Fluoro-1,3-dienes

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Chinese Journal of Chemistry 2019年第10期37卷 1036-1040页

作者： Shengjin Song Huan Liu Lu Wang Chuan Zhu Teck-peng loh Chao Feng Department of Chemistry University of Science and Technology of ChinaHefeiAnhui 230026China Institute of Advanced Synthesis School of Chemistry and Molecular EngineeringJiangsu National Synergetic Innovation Center for Advanced MaterialsNanjing Tech UniversityNanjingJiangsu 211816China Division of Chemistry and Biological Chemistry School of Physical and Mathematical SciencesNanyang Technological University637371Singapore

Herein,we present a strategy for the formation of 2-fluoro-1,3-diene derivatives via rhodium-catalyzed direct C(sp2)-C(sp2) cross-coupling of gem-difluoroalkenes and *** merging Rh(Ⅲ)-catalyzed C(sp2)-H bond activation and nucleophilic addition/F-elimination of gem-difluoroalkene,an efficient defluorinative vinylation reaction is uncovered,which leads to the generation of 2-fluoro-1,3-dienes in moderate to good yields with excellent stereoselectivity under mild *** mechanistic study suggests unique effects of fluorine substituents which allow the reactivity profile not observed with the congeners bearing heavier halides.

关键词： diene catalyzed fluorine

Access to multi-functionalized oxazolines via silver-catalyzed heteroannulation of enamides with sulfoxonium ylides

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Chinese Chemical Letters 2021年第4期32卷 1411-1414页

作者： Rui-Hua Liu Qi-Chao Shan ya Gao Teck-peng loh Xu-Hong Hu Institute of Advanced Synthesis School of Chemistry and Molecular EngineeringNanjing Tech UniversityNanjing 211816China Division of Chemistry and Biological Chemistry School of Physical and Mathematical SciencesNanyang Technological UniversitySingapore 637371Singapore

Disclosed herein is an efficient Ag-catalyzed 4+1 heteroannulation reaction of enamides withα-carbonyl sulfoxonium *** diastereoselective transformation provides a practical access to a diverse range of multi-functionalized oxazoline *** synthetic utility of the resultant tetrasubstituted oxazolines is further demonstrated by a series of useful manipulations into valuable building blocks of pharmaceutical relevance.

关键词： Enamides Sulfoxonium ylides Oxazolines Silver catalysis Heteroannulation

Stereoselective Synthesis of cis-2,5-Disubstituted Pyrrolidines via Copper-Catalyzed Cyclization of Alkenes

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Chinese Journal of Chemistry 2016年第11期34卷 1076-1080页

作者： Sai-Hu Cai Bing-Chao Da Jia-Hui Zhou yun-He Xu Teck-peng loh Department of Chemistry University of Science and Technology of China Hefei Anhui 230026 China DiVision of Chemistry and Biological Chemistry School of Physical and Mathematical Sciences Nanyang Technological University 637371 Singapore

An efficient methodology for the stereoselective synthesis of cis-2,5-disubstituted pyrrolidines using copper catalyst was developed. The corresponding cis-2,5-disubstituted pyrrolidines could be obtained in reasonable yields and with good stereoselectivities in the presence of 4,4＇-di-tert-butyl-2,2＇-bipyridine as ligand and l-methyl-2-pyrrolidinone as solvent.

关键词： stereoselectivity pyrrolidines copper-catalyzed cyclization

Development of catalyst-free carbon-sulfur bond formation reactions under aqueous media and their applications

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Green Synthesis and Catalysis 2022年第4期3卷 309-316页

作者： Min Sun Kang Joycelyn yi Xin Khoo Zhenhua Jia Teck-peng loh Division of Chemistry and Biological Chemistry School of ChemistryChemical Engineering and Biotechnology(CCEB)Nanyang Technological UniversitySingapore 637371Singapore Henan University of Technology 100 Lianhua StZhongyuan DistrictZhengzhou 450001China

Methods for the carbon-sulfur bond formation under catalyst-free,aqueous conditions are extremely useful in organic synthesis and chemical *** laboratory has developed methodologies to construct carbon-thiol bonds,carbon-sulfinic acid bonds,and carbon-disulfide bonds and such methodologies have been widely adopted by other research groups over multidisciplinary *** this article,our work on C-S bond formation in an aqueous solvent and its corresponding applications is summarized.

关键词： Green synthesis Biocompatible Water-based reaction Biologics C-S bond

Indium（Ⅲ） Iodine Catalyzed Strecker Reaction in Water: An Efficient and Environmentally-friendly Method for the Synthesis of a-Aminonitrile via a Three-component Condensation

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Indium（Ⅲ） Iodine Catalyzed Strecker Reaction in Water: An...

Rencent Progress In The Total Synthesis Of Natural Products

中国化学会第四届有机化学学术会议

作者： loh,Teck-peng Key Lab of Organic Synthesis of Jiangsu Province College of Chemistry and Chemical Engineering Suzhou University Suzhou 215006 China Division of Chemistry and Biological ChemistryNanyang Technological UniversitySingapore 637616Singapore

＜正＞α-Aminonitriles are significantly important intermediates for the synthesis of a wide variety of amino acids, amides, diamines and nitrogen-containing heterocycles. Among the numerous methods described for the syntheses of α-aminonitriles, Strecker reaction which proceeded via the addition of HCN to imine proved to be an effective method for the preparation of α-aminonitrile. Recently, modified method using one-pot procedure via three-component condensation of aldehyde, amine and trimethylsilyl cyanide catalyzed by Lewis acids in organic

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Rencent Progress In The Total Synthesis Of Natural Products