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Chinese Journal of Chemistry 2013年第7期31卷 892-900页

作者： lijing wang qilong shen long lu Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China

A highly selective method for the asymmetric formation of trifluoromethyl-substituted α- and β-aminophos- phonates was described. The reaction proceeded with high yields and good to excellent diastereoselectivity. T... 详细信息

关键词： trifluoromethyl aminophosphonate asymmetric fluorine

A Versatile,Electrophilic Reagent for Monofluoromethylthiolation

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Chinese Journal of Chemistry 2023年第18期41卷 2317-2329页

作者： Rui wang long lu qilong shen Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChineseAcademyof Sciences345 Lingling RoadShanghai 200032China

Comprehensive Summary,A new electrophilic monofluoromethylthiolating reagent N-fluoromethylthiophthalimide PhthSCH2F 1 was *** 1 could be readily synthesized from easily available starting materials benzyl mercaptan and CH_(2)FCl in three steps.N-Fluoromethylthiophthalimide 1 is a powerful electrophilic monofluoromethylthiolating reagent that allows the monofluoromethylthiolation of a wide range of nucleophiles including alkynes,aryl/vinyl boronic acids,electron-rich heteroarenes,β-ketoesters and oxindoles,as well as thiols under mild conditions.

关键词： Fluorine Monofluoromethylthiolation Electrophilic Sulfur

Access to Versatile Functionalized Cu(Ⅲ) Complexes Enabled by Direct Transmetalation to Well-Defined Copper(Ⅲ) Fluoride Complex Me_(4)N^(+)[Cu(CF_(3))_(3)F]^(-)

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Chinese Journal of Chemistry 2024年第10期42卷 1107-1113页

作者： Guangyu wang Huaiyuan Li Xuebing Leng long lu qilong shen Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of Sciences345 Lingling LuShanghai 200032China

The invention of a well-defined Cu(Ⅲ)fluoride complex Me_(4)N^(+)[Cu(CF_(3))_(3)(F)]^(-)1 enabled to access a versatile of functionalized Cu(Ⅲ)complexes[Me_(4)N]^(+)[Cu(X)(CF_(3))_(3)]^(-)(X=C_(6)F_(5),C_(6)F_(5)C≡C,CN,Cl,N_(3),^(t)BuOO,SCN,OAc,SAr),many of them for the first *** availability of these complexes allowed us to evaluate the trans-influence order of ligand in Cu(Ⅲ)complexes:Bn>CF_(3)^(-)>C_(6)F_(5)^(-)>N_(3)^(-)>py~CH_(3)^(-)~C_(6)F_(5)C≡C>NO_(2)PhO^(-)~^(t)BuOO^(-)~CH_(3)COO^(-)>F^(-).

关键词： Fluorine Copper Cu(Ⅲ) Cu(Ⅲ)fluoride Trifluoromethyl

Neutral Five-Coordinate Arylated Copper(Ⅲ) Complex: Key Intermediate in Copper-Mediated Arene Trifluoromethylation

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Chinese Journal of Chemistry 2022年第16期40卷 1924-1930页

作者： Guangyu wang Man Li Xuebing Leng Xiaosong Xue qilong shen Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of Sciences345 Lingling LuShanghai200032 China Key Laboratory of Material Chemistry for Energy Conversion and Storage Ministry of EducationHubei Key Laboratory of Bioinorganic Chemistry and Materia MedicaHubei Key Laboratory of Materials Chemistry and Service FailureSchool of Chemistry and Chemical EngineeringHuazhong Universityof Scienceand TechnologyWuhanHubei 430074China

Five-coordinate neutral Cu(Ⅲ)complexes have long been considered as the key intermediates in copper-mediated/catalyzed arene trifluoromethylative reactions,but the identity of these complexes remains ***,we reported,for the first time,the preparation and characterization of these putative complexes[(bpy)Cu(CF_(3))_(2)(C_(6)F_(4)R)]and investigation of their C(sp^(2))-CF_(3) bond-forming reductive *** mechanistic studies including kinetic studies,the effect of temperature and solvents,the effect of the para-substitution of the ligand as well as DFT calculations suggest that C(sp^(2))-CF_(3) reductive elimination process proceeds via synchronous bond-breaking/bond-forming process.

关键词： Cu(Ⅲ) Reductive elimination Trifluoromethyl Mechanism Concerted pathway

Phase-transfer-shuttle generated in situ enables novel SN1-type fluorination of sulfonium ylide with hydrofluoric acid

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Science China Chemistry 2024年

作者： Yisa Xiao Rui wang Zhaoxuan Xu Qunchao Zhao Renyi Pang Tao Dong long lu qilong shen Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic Chemistry University of Chinese Academy Sciences Chinese Academy of Sciences

The development of a nucleophilic fluorination protocol using hydrofluoric acid as the fluoride source represents a long-sought goal in the field of organofluorine chemistry. We report herein the realization of such a reaction that employed alkyl-substituted sulfonium ylides as the substrates. The key to the success of the protocol was attributed to two factors: First, as a Br?nsted base,the ylide was able to be protonated by HFaq, thus serving as a phase-transfer shuttle generated in situ to bring F-from aqueous phase to the organic phase promoting desolvation of fluoride ion. Second, after protonation, a sulfonium salt, a good leaving group, was generated and subsequent attacked by the fluoride to afford the alkyl fluoride. Mechanistic investigation indicates that the reaction occurs via an SN1 pathway. Because of the nature of the cationic intermediate in the reaction, two attractive rearrangement-fluorination approaches including 1,2-aryl migration fluorination and ring-expansion fluorination were disclosed.

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