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Switchable Multicomponent Cyclization Reactions to Access Fluoroalkylated Dihydropyrimidines and Pyrimidines under Solvent-Free Conditions

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Chinese Journal of chemistry 2024年第12期42卷 1394-1398页

作者： Wanqing Zuo Zhizhen Zhu Yu Cheng Lingling Zuo Xiao Geng Zhifang Li Lei Wang College of Material chemistry and Chemical Engineering Key Laboratory of Organosilicon Chemistry and Material TechnologyMinistryof EducationHangzhouNormal UniversityHangzhouZhejiang311121China Advanced Research Institute and School of Pharmaceutical Sciences Taizhou UniversityJiaojiangZhejiang 318000China state Key Laboratory of Organometallic chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai200032China

Comprehensive Summary The development of switchable solvent-free multicomponent reactions to build high-value-added products is an important demand for organic synthesis.Herein,we detailed the successful implementation of a switchable strategy for the construction of diverse 4-fluoroalkyl-1,4-dihydropyrimidines and 4-fluoroalkyl-pyrimidines via a solvent/additive-free[3+2+1]annulation,starting from readily available enamines,trifluoroacetaldehyde hydrate or 1-ethoxy-2,2-difluoroethanol and amidines hydrochloride.This reaction conforms to the concept of green synthesis,and provides a new avenue to access valuable fluorinated heterocycles.

关键词： fluorine chemistry Multicomponent reactions Environmental chemistry Heterocycles Enaminones Amidines

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Iridium(I)-catalyzed deoxgenation of fluoroalkylsulfoxides with dimethyl diazomalonate to access fluoroalkylthioethers

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Chinese Chemical Letters 2022年第11期33卷 4865-4869页

作者： Wenqing Lu Wenlin Li Yicheng Zhou Yongbin Xie Wenbo Chen Shanghai Key Laboratory of Materials Protection and Advanced Materials in Electric Power Shanghai University of Electric PowerShanghai 200090China CAS Key Laboratory of Energy Regulation Materials Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

A new method for the preparation of fluoroalkylthioethers including trifluoromethylthioether and difluoromethylthioether by iridium(Ⅰ)-catalyzed deoxgenation of fluoroalkylsulfoxides with dimethyl diazomalonate was developed.In the reaction system,dimethyl diazomalonate was used as reducing reagent and the corresponding fluoroalkylthioethers were produced through oxygen atom transfer from fluoroalkylsulfoxides to diazomalonate.The protocol featuring effective oxygen atom transfer,mild reaction conditions and good functional groups tolerance offers an alternative strategy for the synthesis of fluoroalkylthioethers.

关键词： fluorine chemistry Trifluoromethylthio Fluoroalkylthio Fluoroalkylsulfoxide Deoxgenation

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Development and Application of Trifluoromethoxylating Reagents

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Chinese Journal of chemistry 2023年第17期41卷 2179-2196页

作者： Yafeng Si Pingping Tang State Key Laboratory and Institute of Elemento-Organic chemistry College of ChemistryNankai UniversityTianjin 300071China

Comprehensive Summary,The trifluoromethoxy functional group has received increasing attention in recent years due to its distinctive properties such as good metabolic stability,appropriate lipophilicity and special electrical properties.Thus,the development of new reagents and new strategies of direct trifluoromethoxylation are attracting the enthusiasm of many fluorine chemical workers.At present,nucleophilic and radical trifluoromethoxylating reagents have made major breakthroughs,greatly promoting the development of trifluoromethoxy chemistry.

关键词： fluorine chemistry Trifluoromethoxylation Nucleophilic Radical Synthetic applications Methodology and Reactions

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A Fruitful Decade of Organofluorine chemistry: New Reagents and Reactions

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CCS chemistry 2022年第8期4卷 2518-2549页

作者： Feng-Ling Qing Xin-Yuan Liu Jun-An Ma Qilong Shen Qiuling Song Pingping Tang Key Laboratory of Organofluorine chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032 Shenzhen Grubbs Institute Department of ChemistryGuangdong Provincial Key Laboratory of CatalysisSouthern University of Science and TechnologyShenzhen 518055 Department of chemistry Tianjin UniversityTianjin 300072 Institute of Next Generation Matter Transformation College of Chemical EngineeringHuaqiao UniversityFujian 361021 State Key Laboratory Institute of Elemento-Organic ChemistryCollege of ChemistryNankai UniversityTianjin 300071

The development of synthetic methods for the introduction of the fluorine atom and fluoroalklyl groups into organic molecules has gained increased attention.Synthetic organic chemists have recently jumped into the field of organofluorine chemistry and have thus made significant contributions.Furthermore,these newly developed methods are typically safer and more effective than the traditional methods.In this review,wewill summarize the representative contributions of new reagents and reactions developed in the past decade.

关键词： fluorination fluoroalkylation reagent reaction fluorine chemistry

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Recent progress in the synthesis of sulfonyl fluorides for SuFEx click chemistry

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Chinese Chemical Letters 2021年第9期32卷 2736-2750页

作者： Tao Zhong Zhida Chen Jitao Yi Gui Lu Jiang Weng Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery School of Pharmaceutical SciencesSun Yat-sen UniversityGuangzhou 510006China

Since the sulfur(Ⅵ)fluoride exchange reaction(SuFEx)was introduced by Sharpless and co-workers in 2014,this new-generation click chemistry has emerged as an efficient and reliable tool for creating modular intermolecular connections.Sulfonyl fluorides,one of the most important sulfur(Ⅵ)fluoride species,have attracted enormous attention in diverse fields,ranging from organic synthesis and material science,to chemical biology and drug discovery.This review aims to introduce seminal and recent progresses on the synthetic methods of sulfonyl fluorides,which include aromatic,aliphatic,alkenyl,and alkynyl sulfonyl fluorides.While not meant to be exhaustive,the purpose is to give a timely overview and insight in this field,and stimulate the development of more efficient synthetic methods of sulfonyl fluorides.

关键词： Click chemistry Sulfur(Ⅵ)fluoride exchange Sulfonyl fluorides fluorine chemistry Synthetic methods

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