A5035495111- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Molecular spectroscopy and chirality
- Supramolecular Chemistry and Complexes
- Chemical Reaction Mechanisms
- Chemical Synthesis and Reactions
- Asymmetric Synthesis and Catalysis
- Molecular Sensors and Ion Detection
- Synthetic Organic Chemistry Methods
- Synthesis and Catalytic Reactions
- Atomic and Subatomic Physics Research
- Chemical Synthesis and Analysis
- Porphyrin and Phthalocyanine Chemistry
- Advanced NMR Techniques and Applications
- Synthesis and characterization of novel inorganic/organometallic compounds
- Synthesis and Reactions of Organic Compounds
- Analytical Chemistry and Chromatography
- Synthesis and Properties of Aromatic Compounds
- Coordination Chemistry and Organometallics
- Asymmetric Hydrogenation and Catalysis
- Organophosphorus compounds synthesis
- DNA and Nucleic Acid Chemistry
- Fluorine in Organic Chemistry
- Organometallic Complex Synthesis and Catalysis
- Photoreceptor and optogenetics research
Université Claude Bernard Lyon 1
2017-2024
Laboratoire de Chimie
2014-2024
École Normale Supérieure de Lyon
2014-2024
Centre National de la Recherche Scientifique
2008-2024
Institut des Sciences Chimiques de Rennes
2015-2019
Université de Rennes
2015-2019
University of Pittsburgh
2019
McGill University
2014-2015
Institut Lavoisier de Versailles
2010-2013
Ludwig-Maximilians-Universität München
2010
Abstract This review article presents how nitrogen‐centred Lewis bases were modified in order to increase their reactivity catalytic processes. As examples, we focus on alcohol acylation and Morita–Baylis–Hilman reactions showcase the fundamental parameters at play transformations initiated by catalysts bearing respectively an active sp 2 or 3 nitrogen atoms. These two aspects are epitomised leading compounds, Steglich base 4‐dimethylaminopyridine (DMAP), 1,4‐diazabicyclo[2.2.2]octane...
Abstract Novel conjugated, pyridyl‐functionalised triazaphospholes with either t Bu or SiMe 3 substituents at the 5‐position of N PC heterocycle have been prepared by a [3+2] cycloaddition reaction and compared structurally related, triazole‐based systems. Photoexcitation 2‐pyridyl‐substituted triazaphosphole gives rise to significant fluorescence emission quantum yield up 12 %. In contrast, all‐nitrogen triazole analogue shows no all. DFT calculations indicate that 2‐pyridyl substituted...
3,4,5-Triamino-substituted pyridines are avid for electrophiles but still willing to give them back. In these compounds three amino groups conjoin their forces into the heterocyclic nitrogen, making it a powerful Lewis base. A short and efficient synthesis is described, origin of its unique activity in nucleophilic organocatalysis rationalized by kinetics thermodynamic quantifications.
Herein, the experimental physicochemical and chiroptical properties of a series phosphahelicenes are reported, focusing on their UV/Vis absorption, luminescence, electronic circular dichroism, optical rotations, circularly polarized luminescence. Furthermore, detailed analysis absorption ECD spectra performed with help quantum-chemical calculations allowed us to highlight general features these helicenic phosphines. Finally, due well-suited electrochemical thermal stability, systems were...
Abstract New heterocyclic derivatives of 9‐azajulolidine have been synthesized and characterized with respect to their nucleophilicity Lewis basicity. The basicity these bases as quantified through theoretically calculated methyl‐cation affinities correlate well the experimentally measured reaction rates for addition benzhydryl cations. All newly pyridines show exceptional catalytic activities in benchmark acylation reactions, which only poorly or parameters. A combination charge geometric...
Rates for the ring-opening of aziridinium and azetidinium ions by DMAP were measured. The four-membered ring appears to be ca. 17,000 times less reactive compared three-membered but is still highly relevant from a synthetic viewpoint. electrophilicity these strained ammonium measured first time.
We report the synthesis and optical resolution of C3-symmetrical tris-aza-cryptophanes anti-3 syn-4, as well study their interaction with xenon via hyperpolarized 129Xe NMR. These molecular cages are close structural analogues two well-known cryptophane-A (1; chiral) cryptophane-B (2; achiral) diastereomers since these new compounds differ only by presence three nitrogen atoms grafted onto same cyclotribenzylene unit. The assignment relative (syn vs anti) absolute configurations was made...
An anti-cryptophane decorated with three aromatic amine and phenol groups shows a high affinity for the cesium thallium cations in LiOH/H2O (0.1 M). The formation of complexes was studied by 133Cs NMR 205Tl spectroscopy at different temperatures. Characteristic signals caged were observed field respect to free present bulk. Isothermal titration calorimetric experiments performed M) NaOH/KCl buffer (pH = 13) allowed us determine parameter complexation ascertain this cryptophane thallium. A...
We report the synthesis of C3-symmetric cryptophanes decorated with three aromatic amine groups on same CTB cap and their interaction xenon. The relative stereochemistry these two stereoisomers syn anti was assessed thanks to determination X-ray structure an intermediate compound. As previously observed tris-aza-cryptophanes analogs anti-1 syn-2 (J. Org. Chem. 2021, 86, 11, 7648–7658), both compounds anti-5 syn-6 show a slow in–out exchange dynamics xenon at 11.7 T. Our work supports idea...
We show here that optically active cryptophane 1 bearing phenol functions can efficiently bind the two enantiomers of 2‐(chloromethyl)oxirane, ethyloxirane, and 2,2′‐bioxirane derivatives in aqueous solution. The binding process is characterized by high‐field H NMR signals are specific to encapsulated species. In all cases, an enantioselective effect was observed a relationship between molecular volume guest constant be established, even though flexibility molecule also seems play role. this...
In this article, we present the synthesis of new cryptophane-type hosts capable binding xenon in aqueous media and that may be useful for development xenon-based magnetic resonance imaging derivatives. The synthetic route proposed was chosen to facilitate both introduction water-solubilizing substituents functionalization host with a single arm showing recognition properties constitute two crucial steps. This made possible by preparing cryptophane-223 derivatives bearing different chemical...
Abstract A novel family of nucleophilic catalysts derived from 4‐(dimethylamino)pyridine (DMAP) is described. The aminopyridine moiety attached to a [2.2]paracyclophane skeleton, giving catalyst with intrinsic planar chirality. Their synthesis described starting aminoparacyclophane 5 in four steps. In the course this preparation, an unprecedented rearrangement involving C–C bond insertion was observed, leading unexpected quinolone‐phenyl[2.2]cyclophane ( 8 ). target 16 obtained enantiopure...
Abstract In 1,1,2,2‐tetrachloroethane‐ d 2 , the 129 Xe NMR spectrum of Xe@cryptophane‐223 complex bearing seven acetate groups (Xe@ 1 complex) shows an unusually broad signal compared with that its congeners (Chapellet, LL. et al. J. Org. Chem . 2015 ;80:6143–6151). To interpret this unexpected behaviour, a H analysis and thorough study chiroptical properties as function nature solvent have been performed. The spectra reveal self‐encapsulation phenomenon takes place in DMSO‐ 6 solvents....
Bromoalkanoate imides undergo intramolecular alkylation to form cyclopentane carboximides using catalytic amounts of magnesium bromide in the presence DBU. Addition PyBox ligands affords products with moderate enantioselectivity.
Abstract The two enantiomers of 2,2′‐bioxirane were synthesized, and their chiroptical properties thoroughly investigated in various solvents by polarimetry, vibrational circular dichroism (VCD), Raman optical activity (ROA). Density functional theory (DFT) calculations at the B3LYP/aug‐cc‐pVTZ level revealed presence three conformers ( G + , − cis ) with Gibbs populations 51, 44, 5% for isolated molecule, respectively. population ratios main modified exhibiting higher dielectric constants...
Abstract The catalytic intramolecular alkylation of oxazolidinone imides is conducted in presence MgBr 2 .OEt combined with a pyridine‐bisoxazoline ligand.