CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis

Rouen, France

CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis

Rouen, France

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Chevalier A.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Renard P.-Y.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Romieu A.,CNRS Molecular Chemistry Institute of Burgundy University | Romieu A.,Institut Universitaire de France
Organic Letters | Year: 2014

A rapid access to a novel class of water-soluble dark quencher dyes was achieved using an azo-coupling reaction between a fluorescent primary arylamine derived from a sulforhodamine 101 scaffold and a tertiary aniline equipped with different bioconjugatable groups. The thus obtained nonfluorescent azo-sulforhodamine hybrids display a broad quenching range spanning the visible to NIR regions. This was demonstrated through the preparation and enzymatic activation of FRET-based fluorogenic substrates of urokinase. © 2014 American Chemical Society.


Besset T.,University of Amsterdam | Besset T.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Gramage-Doria R.,University of Amsterdam | Reek J.N.H.,University of Amsterdam
Angewandte Chemie - International Edition | Year: 2013

Working together: The presence of a remote directing group on terminal 1,1-diaryl and 1,1-dialkyl alkenes led to high and unprecedented enantioselectivity in iridium-catalyzed asymmetric hydrogenation (see scheme). This strategy offers efficient synthetic pathways towards valuable enantiomerically enriched 1,1-diaryl and 1,1-dialkyl alkanes. Moreover, the directing group can be further functionalized. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Tognetti V.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Joubert L.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis
Chemical Physics Letters | Year: 2013

In this Letter, we extend our recent work [J. Chem. Phys. 138 (2013) 024102] on intramolecular O.Y interactions (Y being O, S, or a halogen atom) in the framework of Bader's atoms in molecules theory. The virial field as well as the variation rates of reduced density gradients and exchange energy density at the bond critical points are discussed, and new homogeneity descriptors are introduced. Finally, a fast and accurate method for the evaluation of interaction exchange energy, based on the sole electron density, is proposed. © 2013 Elsevier B.V. All rights reserved.


Bouzbouz S.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis
Synlett | Year: 2011

A very simple sequence of reactions such as cross-·metathesis using two catalysts and allylation to give the chiral hydroxyamide is described. © 2011 Georg Thieme Verlag Stuttgart · New York.


Schneider C.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Masi D.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Couve-Bonnaire S.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Pannecoucke X.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Hoarau C.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis
Angewandte Chemie - International Edition | Year: 2013

A gem of a reaction: The palladium- and copper-catalyzed base-assisted direct C-H fluoroalkenylation of heterocycles 1 with gem-bromofluoroalkenes (E)-2 is reported. This method offers step-economical and stereocontrolled access to valuable trisubstituted heteroarylated monofluoroalkenes (Z)-3. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Loidreau Y.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Besson T.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis
Tetrahedron | Year: 2011

Rapid and efficient generation of CO and NH3 in the reaction mixture via microwave-assisted thermal decomposition of formamide may represent a significant improvement over existing methods for coupling a pyrimidine ring with an aromatic partner. This work aims at alerting readers on the probability to observe interesting phenomena and reactions when this very powerful heating mode is associated with thermally unstable reagents. © 2011 Elsevier Ltd. All rights reserved.


Lee S.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Chataigner I.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Piettre S.R.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis
Angewandte Chemie - International Edition | Year: 2011

Breaking the aromaticity barrier: Nitrobenzene derivatives and other nitroarenes smoothly react at room temperature with an azomethine ylide to yield polycyclic adducts in high yields (see scheme; Bn=benzyl, TFA=trifluoroacetic acid). This unprecedented loss of aromaticity delivers scaffolds prone to a number of potentially interesting derivatizations. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Tognetti V.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Joubert L.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis
Physical Chemistry Chemical Physics | Year: 2014

Density functional theory and Bader's atoms-in-molecules theory share the same primary ingredient: the electron density, which is the fundamental physical observable in quantum chemistry. In this paper, we elaborate on the decomposition of the Kohn-Sham molecular energy in terms of Bader's partition, discussing how Pendás' Interacting Quantum Atoms framework could be adapted to a DFT context. Besides, another bridge between these two theories is built through a general formalism able to generate new local descriptors from any second-order density gradient expansion. These approaches are then applied to two classes of intramolecular bonds: between two electronegative atoms and intramolecular hydrogen bonds, illustrating how fruitful a dialog between both theories can be. © the Partner Organisations 2014.


Dai X.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Cahard D.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis
Advanced Synthesis and Catalysis | Year: 2014

A simple combination of dichloro(para-cymene)ruthenium(II) dimer, a chiral amino alcohol and isopropyl alcohol allowed for in-situ generation of the bifunctional catalyst responsible for the transfer hydrogenation reaction of trifluoromethyl ketimines in excellent yields with high enantioselectivities (up to 93% ee). Herein, we describe the optimization, scope, limitations, and applications of the method. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Sabot C.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Oueis E.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Brune X.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis | Renard P.-Y.,CNRS Organic Chemistry, Bioorganic Chemistry: Reactivity and Analysis
Chemical Communications | Year: 2012

A general and single-step access to polysubstituted 3-hydroxypyridine scaffolds via hetero-Diels-Alder (HDA) reactions between readily prepared 5-ethoxyoxazoles and dienophiles is reported. The HDA reaction, run in the presence of Nd(OTf) 3 at room temperature, was successfully applied to various 5-ethoxyoxazoles showing good functional group tolerance, and led to a straightforward process to obtain useful building-blocks. © 2012 The Royal Society of Chemistry.

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