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Metal-free regioselective construction of 2-aryl-2H-tetrazol-5-yl difluoromethylene phosphonates

Chinese Chemical Letters 2022年第2期33卷 863-866页

作者： Shi-Jing Zhai dominique cahard Fa-Guang Zhang Jun-An Ma Department of Chemistry Tianjin Key Laboratory of Molecular Optoelectronic SciencesFrontiers Science Center for Synthetic Biology(Ministry of Education)and Tianjin Collaborative Innovation Centre of Chemical Science&EngineeringTianjin UniversityTianjin 300072China Joint School of National University of Singapore and Tianjin University International Campus of Tianjin UniversityFuzhou 350207China CNRS UMR 6014 COBRA Normandie UniversitéMont Saint Aignan 76821France

Three bench-stable difluoromethylene phosphonate hydrazones were prepared from simple diethyl(difluoromethyl)phosphonate within two steps in good yields. The [3 + 2] cycloaddition reaction of these diazo precursors with aryl diazonium salts has been accomplished under metal-free conditions with exclusive regioselectivity. This transformation provides practical access to a broad panel of 2-aryl-2 H-tetrazol-5-yl difluoromethylene phosphonates, including the corresponding derivatives of amino acid(phenylalanine) and drug cores(Pomalidomide and Lapatinib fragment).

关键词： Tetrazole Cycloaddition Difluoromethylene phosphonate Regioselectivity Diazonium salt

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State-of-the-Art in Electrophilic Trifluoromethylthiolation Reagents

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Chinese Journal of Chemistry 2016年第5期34卷 445-454页

作者： Helene Chachignon dominique cahard Normandie UniversitY CNRS UMR 6014 COBRA et FR 3038 Universite de Rouen INSA Rouen. 1 rue Tesniere 76821 Mont Saint-Aignan Cedex France

The trifluoromethylthio group （SCF3） is a fluorine chemotype that has experienced a strong acceleration of in- terest in the recent years. It is particularly true of the construction of new fluorinated architectures by electrophilic trifluoromethylthiolation. The spread of knowledge was already very active in this research domain in the sixties; however, gaseous and highly toxic trifluoromethanesulfenyl chloride （CF3SC1） was the only reagent available at that time. Nowadays, one really can speak of a revival in the field thanks to the rapid development of a wide pano- ply of reagents that are stable and easy to handle. This review provides a historical perspective of the development of shelf-stable electrophilic trifluoromethylthiolation reagents.

关键词： fluorine sulfur electrophilic addition synthetic methods

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Fluorine Effects in Asymmetric Hydrogen Atom Transfers

Fluorine Effects in Asymmetric Hydrogen Atom Transfers

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中国化学会第十五届全国氟化学会议

作者： dominique cahard CNRS – UMR 6014 C.O.B.R.A.– Normandie Université

The subtle effects of fluorine atom(s) on the course of asymmetric hydrogen atom transfer reactions will be presented. In the synthesis of fluorinated molecules, it is instructive to understand the various effects of fluorine and to provide a comparison with the chemistry of non-fluorinated analogue molecules. Through a series of examples from my laboratory, I will showcase the role of fluorine, its impact on the mechanism of a reaction, on the conformation of a substrate, and on the reactivity of stereolabile compounds.

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Asymmetric Hydrogen Atom Transfer Reaction of Prostereogenic Trifluoromethylated Compounds

Asymmetric Hydrogen Atom Transfer Reaction of Prostereogenic...

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中国化学会第十四届全国氟化学会议

作者： dominique cahard CNRS UMR 6014 C.O.B.R.A. Normandy University

＜正＞The synthesis of enantiopure molecules featuring a fluorine atom or a fluorinated motif at a stereogenic carbon centre has stimulated considerable *** subtle effects of fluorine atom（s）on the course of asymmet...

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Stereoselective Synthesis of Fluoroalkene Dipeptide Mimics

Stereoselective Synthesis of Fluoroalkene Dipeptide Mimics

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氟化学与美好生活——中国化学会第十一届全国氟化学会议

作者： Camille Pierry Samuel Couve-Bonnaire Xavier Pannecouche dominique cahard UMR CNRS 6014 C.O.B.R.A. Universite et INSA de Rouen76130 Mont Saint Aignan

＜正＞Peptides are potential therapeutic agents but their applications have largely been limited by several factors that include rapid degradation by peptidases and a poor cell *** the years,research has overcome some of these limitations with *** this context,our laboratory is interested in the development of new fluoropeptidomimetics aiming at circumventing common problems associated with *** this purpose,the fluoroalkene motif[CF=CH]can act as an effective peptide bond mimic due to steric and electronic similarities（Figure 1）.

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Synthesis of β-SCF3 α-Amino Acids and β-SCF3 Amines by Nucleophilic Trifluoromethylthiolation of Cyclic Sulfamidates

Synthesis of β-SCF3 α-Amino Acids and β-SCF3 Amines by Nu...

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中国化学会第十四届全国氟化学会议

作者： Jun-Liang Zeng Hélène Chachignon Jun-An Ma dominique cahard UMR 6014 CNRS C.O.B.R.A. Normandie Université Department of Chemistry Tianjin Key Laboratory of Molecular Optoelectronic Sciences Tianjin University and Collaborative Innovation Center of Chemical Science and Engineering

The trifluoromethylthio group SCF is an emergent organofluorine substituent present in a number of potential drugs and ***,we have witnessed the passionate upsurge of interest in the construction of the SCF motif and ...

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