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Pentacoordinate Phosphoranes as Versatile Reagents in fluoroalkylation Reactions

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CCS Chemistry 2024年第1期6卷 165-176页

作者： Huanhuan Song Weihao Li Xiaoying Wang Kaiteng Wang Jingwen Li Shuai Liu Pin Gao Xin-Hua Duan Jinbo Hu Mingyou Hu School of Chemistry Engineering Research Center of Energy Storage Materials and DevicesMinistry of EducationXi’an Key Laboratory of Sustainable Energy Material ChemistryXi’an Jiaotong UniversityXi’an 710049 Key Laboratory of Organofluorine Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai 200032

A general method for the synthesis of bench-stable bis(difluoromethyl)pentacoordinate phosphoranes has been developed.The reaction is rapid,operationally simple,and easily scalable.The pentacoordinate phosphoranes can generate both difluoromethyl radical(·CF_(2)H)and difluorocarbene(:CF_(2))intermediates.Thus,a variety of fluoroalkylation transformations havebeen achieved by·CF_(2)H,such asoxidativedifluoromethylation of electron-deficient heterocycles,nickel/photoredox dual-catalyzed difluoromethylation of aryl bromides,and photoredox difluoromethylation of alkenes,or by:CF_(2),such as gem-difluorocyclopropanation of alkenes,base-promoted difluoromethylation of heteroatom nucleophiles,Pd-catalyzed difluoromethylation of arylboronic acids,and Cu-mediated trifluoromethylation of aryl iodides(via:CF_(2) and recombined CF_(3)-).These fluoroalkylation methods have been successfully applied to late-stage fluoroalkylation of drugs and drug-like molecules.

关键词： pentacoordinate phosphorane difluoromethyl radical difluorocarbene difluoromethylation fluoroalkylation

MnBr_(2)catalyzed regiospecific oxidative Mizoroki-Heck type reaction

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Chinese Chemical Letters 2022年第5期33卷 2391-2396页

作者： Xiang Chen Zhihong Zhu Shanshan Liu Yi-Hung Chen Xiao Shen Institute for Advanced Studies Engineering Research Center of Organosilicon Compounds&MaterialsMinistry of EducationWuhan UniversityWuhan 430072China

Herein, we report an unprecedented regiospecific oxidative Mizoroki-Heck type reaction for the synthesis of α-difluoromethyl homoallylic alcohols. The reaction shows broad substrate scopes and high functional group tolerance. Late-stage functionalization of complex biologically active molecules demonstrates the synthetic potential of this transformation. Mechanistic study supports the involvement of MnBr_(2) catalyzed radical 1,2-silyl transfer.

关键词： fluoroalkylation Mizoroki-Heck Mn catalysis Radical 1,2-silyl transfer Homoallylic alcohols

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Selective Ni-catalyzed cross-electrophile coupling of alkynes,fluoroalkyl halides,and vinyl halides

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Chinese Chemical Letters 2022年第8期33卷 4074-4078页

作者： Yubei Dai Fang Wang Shengqing Zhu Lingling Chu State Key Laboratory for Modification of Chemical Fibers and Polymer Materials Center for Advanced Low-Dimension MaterialsCollege of ChemistryChemical Engineering and BiotechnologyDonghua UniversityShanghai 201620China

We report a Ni-catalyzed three-component cross-electrophile coupling of alkynes with alkenyl halides and fluoroalkyl halides to generate fluoroalkyl-incorporated 1,3-dienes.This mild and operationally simple protocol is distinguished by its broad substrate scope and excellent chemo-,regio-,and stereo-selectivity,offering a new and organometallic agent-free platform for the construction of fluoroalkyl-incorporated diene motifs.Preliminary mechanistic studies have been conducted to probe the potential reaction pathway.

关键词： fluoroalkylation Cross-electrophile coupling Nickel catalysis Difunctionalization Alkynes

STUDIES ON fluoroalkylation AND FLUOROALKOXYLATION——A NOVEL METHOD OF fluoroalkylation OF ALKENES CATALYSED BY ZINC

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Chinese Science Bulletin 1988年第22期33卷 1866-1868页

作者：陈庆云杨震宇裘再明 Shanghai Institute of Organic Chemistry Academia Sinica

Ⅰ. INTRODUCTION Perfluoroalkylation of alkenes is one of the most important methods for industrial as well as laboratory syntheses of a variety of organofluorine compounds. It is usually induced by light, heat or radical initiators. A few of transition metals and their complexes have been shown to be able to catalyse the addition reaction

关键词： perfluoroalkyl iodide alkene electron transfer zinc fluoroalkylation

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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

STUDIES ON fluoroalkylation AND FLUOROALKOXYLATION 17.A NEW METHOD FOR PREPARATION OF 2-FLUOROALKYL PYRROLE

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有机化学 1987年第1期 45-46页

作者： Chen Qingyun~* Qiu Zaiming (Shanghai Institute of Organic Chemistry,Academia Sinica,Shanghai)

The examples for fluoroalkylating heteroaromatic compounds are rather few.Wak-selman et.***.reported the reaction Of perfluoroalkyl iodides with N-methyl pyrroleunder thermal conditions,but failed for pyrrole tself.How... 详细信息

关键词： fluoroalkyl iodide pyrrole radical reaction fluoroalkylation

New Reagents for （CF2）n Transfer and the Construction of Fluoroalkyl-Containing Rings

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New Reagents for （CF2）n Transfer and the Construction of F...

Efficient Metal-free One-pot Synthesis of Fluoroalkylated Quinoxalines

中国化学会全国第十一届有机合成化学学术研讨会

作者： Peter Kaplan Bo Chen Siqi Yu Long Xu Katherine McGarry David A.Vicic Department of Chemistry Lehigh UniversityBethlehemPA 18015 USA

The preparation of a new series of dinuclear zinc reagents is reported（eqs 1 and 2）.Unlikeα,ω-difunctionalized perfluoroalkyl di-Grignard reagents,which have a half-life of only two hours at -50℃in THF,we observed that 87% of the dizinc reagents remained in acetonitrile solution after 300 h at room temperature.We demonstrate that the reagents can be used to prepare novel fluoroorganics containing either perfluoroalkyl ring systems or perfluoroalkyl linked arenes under relatively mild conditions（eqs 3 and 4）.We also show that these zinc reagents can be used to transmetalate nickel to form monocuclear metallacycles.Different reaction conditions are needed for different chain lengths because in some instances the perfluoroalkylations are competitive with unusual dicuprate formation.We also present results demonstrating that perfluoroalkyl-based metallacycles are exceptionally effective at stabilizing high valent metal complexes.

关键词： fluoroalkylation Fluorine Copper Zinc

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Efficient Metal-free One-pot Synthesis of Fluoroalkylated Qu...