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Nucleophilic trifluoromethylation with CFH/LiHMDS:probing the nucleophilic reactivity of LiCFspecies

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Science China Chemistry 2024年

作者： Yangfan Liu Xiu Wang chuanfa ni Jinbo Hu College of Chemistry Central China Normal University Key Laboratory of Fluorine and nitrogen Chemistry and Advanced Materials Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of Sciences Chinese Academy of Sciences

The nucleophilic trifluoromethylation involving trifluoromethyllithium（LiCF3） species has been an open question since Haszeldine attempted to prepare LiCF3in 1949. Indeed, LiCF3has been used for electrophilic difluoromethylene transfer processes（via elimination of fluoride ions） since 2010. Herein, we demonstrated that by using a polar solvent such as dimethylformamide（DMF） or hexamethylphosphoramide（HMPA） as the lithium chelator, the in situ deprotonation of fluoroform（HCF3） with lithium hexamethyldisilazide（LiHMDS） could generate a tamed LiCF3species that is sufficiently persistent to undergo nucleophilic trifluoromethylation reaction. The nucleophilic reactivity of LiCF3species was probed with several electrophiles,including arylsulfonyl fluorides, diaryl ketones, and silyl chlorides. The synthetic utility of this method is demonstrated with the efficient synthesis of highly valuable triflones that are otherwise difficult to synthesize from HCF3using potassium or sodium bases. This work not only showcases a new protocol for the utilization of fluoroform（an industrial waste with high global warming potential） as the trifluoromethylation reagent, but also provides intriguing insights into the harnessing of nucleophilic reactivity of the transient LiCF3species.

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Copper-Mediated Di- and Monofluoromethanesulfonylation of Arenediazonium Tetrafluoroborates： Probing the Fluorine Effect

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Chinese Journal of Chemistry 2018年第3期36卷 206-212页

作者： Bo Xing chuanfa ni Jinbo Hu Key Laboratory of Organofluorine Chemistry Center for Excellence in Molecular Synthesis Shanghai Institute of Organic Chemistry University of Chinese Academy of Sciences Chinese Academy of Sciences 345Lingling Lu Shanghai 200032 China

A copper-mediated di- and monoffuoromethanesulfonylation of arenediazonium tetrafluoroborates using di- and monofluoromethanesul- finate reagents provides aryl difluoromethyl （or monofluoromethyl） sulfones in 8ood yields. It was found that the relative reactivity of these sodium fluoroalkanesulfinates in the present reactions decreases in the followin8 order： CH2FSO2Na 〉 CF2HSO2Na 〉 CF3SO2Na.

关键词： difluoromethanesulfonylation fluoromethanesulfonylation arenediazonlum sodium sulfinate fluorine effect

Highly Stereoselective and One-Pot Synthesis of Tetra-substituted Monofluoroalkenes with Aldehydes and Fluorobis（phenylsulfonyl）methane

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Chinese Journal of Chemistry 2013年第7期31卷 878-884页

作者： Xiao Shen chuanfa ni Jinbo Hu Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai 200032 China

A highly stereoselective synthesis of tetrasubstituted monofluoroalkenes with aldehydes and fluorobis（phenyl- sulfonyl）methane （FBSM） in one pot has been developed. The reaction was amenable topara- and meta-substituted aryl aldehydes, 2-naphthaldehyde, and cinnamaldehyde, giving phenylsulfonyl-substituted monofluoroalkenes in 40%--86% yields with 98/2- 99/1 Z/E ratios. The presence of the sulfonyl group enables the further transformation of the products into more useful monofluoroalkenes.

关键词： olefination aldehydes nucleophilic addition sulfones fluorine

China's flourishing synthetic organofluorine chemistry:innovations in the new millennium

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National Science Review 2017年第3期4卷 303-325页

作者： Qinghe Liu chuanfa ni Jinbo Hu Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences

The new millennium has witnessed the rapid development of synthetic organofluorine chemistry all over the world, and chemists in China have made significant contributions in this field. This review aims to provide a brief introduction to China’s primary innovations from 2000 to early 2017, covering fluorination,fluoroalkylation, fluoromethylthiolation, fluoroolefination and polyfluoroarylation, as well as synthesis with fluorinated building blocks. Recent advances in the chemistry of difluorocarbene and the chemistry of carbon–fluorine bond activation are also discussed. As a conclusion, the review ends with some personal perspectives on the future development of China’s synthetic organofluorine chemistry.

关键词： fluorine organic chemistry synthetic methods fluorination trifluoromethylation trifluoromethylthiolation difluoromethylation difluoroalkylation fluoromethylation fluoroolefination

Nucleophilic Difluoro(phenylsulfonimidoyl)methylation of Unactivated Alkyl Bromides with PhSO(NTBS)CF_(2)H: Facile Entry into gem-Difluoroalkenes

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Chinese Journal of Chemistry 2014年第8期32卷 703-708页

作者： Xiao Shen Qinghe Liu chuanfa ni Jinbo Hu Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 200032China

An efficient nucleophilic difluoro(phenylsulfonimidoyl)methylation of unactivated primary alkyl bromides with PhSO(NTBS)CF_(2)H has been *** is particularly remarkable that,when 1.5 *** alkyl bromides are used,the substitution products are obtained in moderate to excellent *** prepared difluoro(phenylsulfonimidoyl)methylated alkanes can be readily transformed to gem-difluoroalkenes via base-mediatedβ-elimination reaction.

关键词： nucleophilic fluoroalkylation β-elimination difluoroalkene sulfoximine

Pentafluoroethylbenziodoxole （BIX-C2Fs）： A Shelf-Stable Reagent for Pentafluoroethylation of β-Ketoesters and Arylboronic Acids

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Chinese Journal of Chemistry 2016年第7期34卷 662-668页

作者： Jiansheng Zhu Yuguang Li chuanfa ni Qilong Shen Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organie Chemistry Chinese Academy of Sciences Shanghai 200032 China

An improved method for the preparation of pentafluoroethylating reagent pentafluoroethyl-substituted benzio- doxole （BIX-C2Fs） was described. Under mild conditions, BIX-C2F5 was able to react with β-ketoesters or a... 详细信息

关键词： fluorine pentafluoroethyl hypervalent electrophilic cross-coupling

Switching from 2-pyridination to difluoromethylation:ligand-enabled nickel-catalyzed reductive difluoromethylation of aryl iodides with difluoromethyl 2-pyridyl sulfone

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中国科学:化学英文版 2023年第10期66卷 2785-2790页

作者： Wei Du Qinyu Luo Zhiqiang Wei Xiu Wang chuanfa ni Jinbo Hu Key Laboratory of Organofluorine Chemistry Shanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai 200032China

The divergent reductive cross-coupling with an ambident electrophile is ***,we demonstrated a nickel-catalyzed reductive 2-pyridination of aryl iodides with difluoromethyl 2-pyridyl sulfone(2-Py SO_(2)CF_(2)H)via selective C(sp^(2))-S bond cleavage of the sulfone by using a phosphine *** this communication,we report a novel nickel-catalyzed reductive coupling of aryl iodides and 2-Py SO_(2)CF_(2)H reagent,which constitutes a new method for aromatic *** use of a tridentate terpyridine ligand is pivotal for the selective C(sp^(3))-S bond cleavage of the *** method employs readily available nickel catalyst and 2-Py SO_(2)CF_(2)H as the difluoromethylation reagent,providing a facile access to difluoromethylarenes under mild reaction conditions without pre-generation of arylmetal reagents.

关键词： nickel catalysis difluoromethylation 2-PySO_(2)CF_(2)H reductive cross-coupling

Pentafluoroethylation of Arenediazonium Tetrafluoroborates Using On-Site Generated Tetrafluoroethylene

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Chinese Journal of Chemistry 2019年第11期37卷 1131-1136页

作者： Bo Xing Lingchun Li chuanfa ni Jinbo Hu Key Laboratory of Organofluorine Chemistry Centerfor Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of Sciences345 Ling Ling RoadShanghai 200032China

Background and Originality Content Scheme I Aromatic pentafluoroethylation using TFE and CsF Perfluoroalkylated compounds are of great interest in pharmaceutical,agrochemical and material research and industry.[1]In this context,numerous efforts have been devoted to developing novel methods for the introduction of trifluoromethyl group(CF3)into organic aromatic compounds.[2]However,the similar pentafluoroethylation processes are still underexploited.[3] Currently available aromatic pentafluoroethylation methods mainly rely on transition-metal-mediated cross-coupling of aryl halides131 or aryl-boron compounds,141 and C-H functionalization of arenes.

关键词： compounds. aromatic devoted

Fluoro-Hydroxylation of gem-Difluoroalkenes:Synthesis of 18O-labeled α-CF3 Alcohols

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Chinese Journal of Chemistry 2018年第12期36卷 1202-1208页

作者： Jingyu Hu Yide Yang Zhengzhao Lou chuanfa ni Jinbo Hu Key Laboratory of Organofluorine Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of Sciences345 Lingling LuShanghai 200032China School of Physical Science and Technology ShanghaiTech University100 Haike RoadShanghai 201210China

In this paper, a fluoro‐hydroxylation of gem ‐difluoroalkenes is demonstrated. This protocol uses sequential electrophilic fluorination with Selectfluor and nucleophilic hydroxylation with H 2 18 O, which can be used to prepare 18 O‐labeled α‐CF 3 alcohols from gem ‐difluorostyrenes. The reaction is typically carried out at room temperature within 4 h in good to excellent yields. Other nucleophiles (besides H 2 18 O), such as alcohols, carboxylic acid, acetonitrile and N,N ‐dimethylformamide, are also suitable for this difunctionalization of gem ‐difluoroalkenes.

关键词： gem‐difluoroalkene difunctionalization electrophilic fluorination 18O‐labeling trifluoromethyl carbinol