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1. Green synthesis of (R)-3-hydroxy-decanoic acid and analogs from levoglucosenone: a novel access to the fatty acid moiety of rhamnolipids

Author

Enzo Petracco, Amandine L. Flourat, Marie-Charlotte Belhomme, Stéphanie Castex, Fanny Brunissen, Fanny Brunois, Aurélien A. M. Peru, Florent Allais, and Arnaud Haudrechy

Subjects
crop protection agent, cross-coupling, green chemistry, levoglucosenone, Michael addition, Chemistry, QD1-999
Abstract

Rhamnolipids (RLs) are highly valuable molecules in the cosmetic, pharmaceutic, and agricultural sectors with outstanding biosurfactant properties. In agriculture, due to their potential to artificially stimulate the natural immune system of crops (also known as elicitation), they could represent a critical substitute to conventional pesticides. However, their current synthesis methods are complex and not aligned with green chemistry principles, posing a challenge for their industrial applications. In addition, their bioproduction is cumbersome with reproducibility issues and expensive downstream processing. This work offers a more straightforward and green access to RLs, crucial to decipher their mechanisms of action and design novel potent and eco-friendly elicitors. To achieve this, we propose an efficient seven-step synthetic pathway toward (R)-3-hydroxyfatty acid chains present in RLs, starting from cellulose-derived levoglucosenone, with Michael addition, Baeyer–Villiger oxidation, Bernet–Vasella reaction, and cross-metathesis homologation as key steps. This method allowed the production of (R)-3-hydroxyfatty acid chains and derivatives with an overall yield ranging from 24% to 36%.

Published
2024
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3. A stereo-electronic interpretation of a challenging orthoamide Overman rearrangement rationalized by molecular modelling

Author

Judith Juvin, Victor Malherbe, Marie-Charlotte Belhomme, Stéphanie Castex, Agathe Martinez, Hassan Khartabil, and Arnaud Haudrechy

Subjects
Materials Chemistry, General Chemistry, Catalysis
Abstract

The Overman rearrangement difficulties are tentatively explained using stereo-electronic considerations, helping chemists to understand their troubles in this process.

Published
2022

4. Un bon croquis vaut mieux qu’un long discours ? / A good sketch is better than a long speech?

Author

Judith Juvin, Marie-Charlotte Belhomme, Stéphanie Castex, Christophe Bliard, and Arnaud Haudrechy

Abstract

Napoleon Bonaparte once said, “A good sketch is better than a long speech”. Though an ardent promoter of beet sugar production, Napoleon could never have imagined that he was describing the thorny problem of the stereochemical representation of sugars. Drawing the structure of a sugar molecule (also called “carbohydrate”) means addressing the challenge of unambiguously transcribing a three-dimensional reality into a bi-dimensional representation as accurately as possible. Since Emil Fischer's initial proposals, several methods have been suggested, with their advantages and drawbacks. Consequently, selecting a particular approach is far from inconsequential and involves numerous pitfalls. The objective of this document is to raise awareness of the subtleties of sugar molecules representations.

Published
2021

5. Sugars: Intramolecular Dehydration of Hexoses

Author

Marie-Charlotte Belhomme, Arnaud Haudrechy, and Stéphanie Castex

Subjects
Chemistry, Intramolecular force, medicine, Dehydration, medicine.disease, Medicinal chemistry
Published
2021

6. Un bon croquis vaut mieux qu’un long discours ?

Author

Judith Juvin, Marie-Charlotte Belhomme, Stéphanie Castex, Christophe Bliard, Arnaud Haudrechy, bliard, christophe, Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), and Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
dessins, tridimensional, [CHIM.ORGA]Chemical Sciences/Organic chemistry, [CHIM.OTHE] Chemical Sciences/Other, tridimensionnel sugars, [CHIM.OTHE]Chemical Sciences/Other, sucres, [CHIM.ORGA] Chemical Sciences/Organic chemistry, drawings
Abstract

Napoleon Bonaparte once said, “A good sketch is better than a long speech”. Though an ardent promoter of beet sugar production, Napoleon could never have imagined that he was describing the thorny problem of the stereo- chemical representation of sugars. Drawing the structure of a sugar molecule (also called “carbohydrate”) means addressing the challenge of unambiguously transcribing a three-dimensional reality into a bi-dimensional representation as accurately as possible. Since Emil Fischer's initial proposals, several methods have been suggested, with their advantages and drawbacks. Consequently, selecting a particular approach is far from inconsequential and involves numerous pitfalls. The objective of this document is to raise awareness of the subtleties of sugar molecules representations., En disant « Un bon croquis vaut mieux qu'un long discours », Napoléon Bonaparte, pourtant promoteur de la production de sucre de betterave, n'imaginait sans doute pas contribuer au débat sur la représentation stéréochimique des sucres. Dessiner la structure d'une molécule de sucre (en anglais, la terminologie anachronique « hydrate de carbone » subsiste parfois) impose de transcrire, le plus fidèlement possible et sans ambiguïté, une correspondance entre une réalité tridimensionnelle et une représentation bidimensionnelle. Depuis les propositions initiales d'Emil Fischer, plusieurs méthodes ont été présentées. Cet article vise à faire prendre conscience de la subtilité des représentations isomériques des molécules de sucres.

Published
2021

7. 'Sugar Mapping', an Easy-To-Use Visual Tool To Help the Synthetic Chemist Identify Carbohydrate Stereochemical Relationships

Author

Stéphanie Castex, Arnaud Haudrechy, Marie Charlotte Belhomme, Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), and Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, Science instruction, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 05 social sciences, 050301 education, Pentose, General Chemistry, Carbohydrate, Chemist, 01 natural sciences, 0104 chemical sciences, 3. Good health, Education, chemistry, Organic chemistry, Sugar, 0503 education, Visual tool, ComputingMilieux_MISCELLANEOUS
Abstract

A “map” is presented to describe the different stereochemical relationships among carbohydrates, in both the hexose and pentose series. When implemented, it allows chemistry students, teachers, and researchers to readily identify different sugars’ stereochemical interconnections. It may also help orient chemists toward retrosyntheses, in which carbohydrates are used as starting material goals.

Published
2019

8. Copper-Catalyzed Innate Ethoxycarbon­yldifluoromethylation of Electron-Rich ­Arenes

Author

Alexandre Bayle, Marie-Charlotte Belhomme, Xavier Pannecoucke, and Thomas Poisson

Subjects
Chemistry, Organic Chemistry, Copper catalyzed, Fluorine, Organic chemistry, Moiety, Regioselectivity, chemistry.chemical_element, Homogeneous catalysis, Physical and Theoretical Chemistry, Electrophilic aromatic substitution
Abstract

We report the direct introduction of the CF2CO2Et moiety into electron-rich arenes. The copper-catalyzed process uses commercially available and inexpensive BrCF2CO2Et as a fluorinated building block. This radical-free reaction proceeds smoothly to give the desired difluoromethylated arenes in modest to good yields with a Friedel–Crafts-type regioselectivity. The direct introduction of α,α-difluoromethylated amides was also investigated, and this gave the corresponding difluoromethylated arenes, albeit in moderate yields. This method represents the first transition-metal-catalyzed direct introduction of a functionalized fluorinated moiety into electron-rich arenes.

Published
2015

9. Copper-Catalyzed Direct Arylation of Cyclic Enamides Using Diaryliodonium Salts

Author

Xavier Pannecoucke, Thomas Poisson, Marie-Charlotte Belhomme, Nicolas Gigant, Isabelle Gillaizeau, Laetitia Chausset‐Boissarie, Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), and Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Organic Chemistry, chemistry.chemical_element, Regioselectivity, 010402 general chemistry, 01 natural sciences, Biochemistry, Copper, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Functional group, Copper catalyzed, Organic chemistry, Physical and Theoretical Chemistry
Abstract

International audience; A convenient method for the copper(II)-catalyzed direct arylation of cyclic and nonaromatic enamides using diaryliodonium salts has been developed. The reaction demonstrates large functional group tolerance, good yields, and total regioselectivity with a C(3)-functionalization. The synthetic potential of this coupling was explored by using a range of readily accessible diaryliodonium salts and enamides.

Published
2012

10. ChemInform Abstract: Formation of C(sp3)-C(sp3) Bonds by Palladium Catalyzed Cross-Coupling of α-Diazoketones and Allylboronic Acids

Author

Dong Wang, Kálmán J. Szabó, and Marie-Charlotte Belhomme

Subjects
inorganic chemicals, Coupling (electronics), Allylic rearrangement, Chemistry, chemistry.chemical_element, General Medicine, Medicinal chemistry, Redox, Catalysis, Palladium
Abstract

Palladium catalyzed cross-coupling of allylboronic acids with α-diazoketones was studied. The reaction selectively affords the linear allylic product. The reaction proceeds with formation of a new C(sp3)–C(sp3) bond. The reaction was performed without an external oxidant, likely without the Pd-catalyst undergoing redox reactions.

Published
2016

11. Formation of C(sp(3))-C(sp(3)) Bonds by Palladium Catalyzed Cross-Coupling of α-Diazoketones and Allylboronic Acids

Author

Marie-Charlotte, Belhomme, Dong, Wang, and Kálmán J, Szabó

Abstract

Palladium catalyzed cross-coupling of allylboronic acids with α-diazoketones was studied. The reaction selectively affords the linear allylic product. The reaction proceeds with formation of a new C(sp(3))-C(sp(3)) bond. The reaction was performed without an external oxidant, likely without the Pd-catalyst undergoing redox reactions.

Published
2016

12. ChemInform Abstract: Copper-Catalyzed Cross-Coupling of Allylboronic Acids with α-Diazoketones

Author

Dong Wang, Marie-Charlotte Belhomme, Arindam Das, and Kálmán J. Szabó

Subjects
chemistry.chemical_compound, Allylic rearrangement, chemistry, organic chemicals, Functional group, Copper catalyzed, food and beverages, Regioselectivity, General Medicine, Medicinal chemistry
Abstract

Copper-catalyzed cross-coupling of substituted allylboronic acids with α-diazoketones was studied. This allylation reaction is highly regioselective, providing the branched allylic product. The process involves creation of a new C(sp3)–C(sp3) bond by retaining the keto functional group of the α-diazoketone precursor.

Published
2016

13. Copper-Catalyzed Cross-Coupling of Allylboronic Acids with α-Diazoketones

Author

Dong Wang, Arindam Das, Marie-Charlotte Belhomme, and Kálmán J. Szabó

Subjects
chemistry.chemical_compound, Allylic rearrangement, Chemistry, organic chemicals, Organic Chemistry, Functional group, Copper catalyzed, food and beverages, Regioselectivity, Physical and Theoretical Chemistry, Biochemistry, Medicinal chemistry
Abstract

Copper-catalyzed cross-coupling of substituted allylboronic acids with α-diazoketones was studied. This allylation reaction is highly regioselective, providing the branched allylic product. The process involves creation of a new C(sp(3))-C(sp(3)) bond by retaining the keto functional group of the α-diazoketone precursor.

Published
2015

16. Recent Progress toward the Introduction of Functionalized Difluoromethylated Building Blocks onto C(sp2) and C(sp) Centers

Author

Xavier Pannecoucke, Thomas Poisson, Marie-Charlotte Belhomme, Tatiana Besset, Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), and ANR-11-LABX-0029

Subjects
010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, General Chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 010402 general chemistry, 01 natural sciences, Catalysis, 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Organic chemistry, [CHIM.CHEM]Chemical Sciences/Cheminformatics
Abstract

International audience; Fluorine chemistry is a field undergoing tremendous expansion. Although much attention has been paid to the introduction of the fluorine atom and the CF3 group, less interest has been devoted to the introduction of functionalized fluorinated building blocks, in sharp contrast with the high versatility of the fluorinated products. In this Minireview, the most relevant methods for the introduction of difluoromethylated building blocks are summarized. Access todifluoromethylated arenes, alkenes, and alkynes is highlighted and special attention is paid to explanation of the reaction mechanism.

Published
2015

17. ChemInform Abstract: Copper-Mediated Direct Functionalization of Unsaturated C-C Bonds with Ethyl Bromo(difluoro)acetate: A Straightforward Access to Highly Valuable Difluoromethylated Alkenes

Author

Xavier Pannecoucke, Delphine Dru, Thomas Poisson, Tatiana Besset, Dominique Cahard, Marie-Charlotte Belhomme, and Heng-Ying Xiong

Subjects
chemistry.chemical_classification, Direct route, Glycal, chemistry, Copper mediated, Halogenation, Organic chemistry, Surface modification, General Medicine
Abstract

A copper-mediated fluorofunctionalization of alkenes and alkynes has been developed. This method provides ready access to trisubstituted difluoromethylated olefins (from dihydropyrans, glycal derivatives, or terminal alkynes) or to tetrasubstituted olefins (from disubstituted alkynes). The products were obtained in good to high yields with acceptable E/Z selectivities. Finally, a first direct route to difluoromethylated alkynes is reported, albeit with low yields.

Published
2014

18. ChemInform Abstract: Copper-Catalyzed Olefinic C-H Difluoroacetylation of Enamides

Author

Marie-Charlotte Belhomme, Isabelle Gillaizeau, Gilles Caillot, Xavier Pannecoucke, Jeremy Dufour, Laurence Grimaud, and Thomas Poisson

Subjects
Chemistry, Copper catalyzed, Regioselectivity, General Medicine, Medicinal chemistry
Abstract

The regioselective Cu-catalyzed radical free synthesis of β-difluoroester substituted enamides is described.

Published
2014

19. Copper-Catalyzed Direct C‑2 Difluoromethylation of Furans and Benzofurans: Access to C‑2 CF2H Derivatives

Author

Xavier Pannecoucke, Marie-Charlotte Belhomme, Thomas Poisson, Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), and Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Molecular Structure, 010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Iodides, 010402 general chemistry, Methylation, 01 natural sciences, Catalysis, 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Copper catalyzed, Organic chemistry, Moiety, Furans, Copper, ComputingMilieux_MISCELLANEOUS, [CHIM.CHEM]Chemical Sciences/Cheminformatics, Benzofurans
Abstract

We report herein the first copper-catalyzed C-2 difluoromethylation of furans and benzofurans. The developed methodology allows the selective introduction of the CF2CO2Et moiety at C-2 using CuI as a catalyst. This process was applied to a broad range of furans and benzofurans, giving the functionalized products in moderate to good yields. The resulting products were then decarboxylated to afford the highly valuable C-2-CF2H-substituted furans and benzofurans in good yields.

Published
2014

20. Copper-Mediated Direct Functionalization of Unsaturated C–C Bonds with Ethyl Bromo(difluoro)acetate: A Straightforward Access to Highly Valuable Difluoromethylated Alkenes

Author

Heng-Ying Xiong, Xavier Pannecoucke, Dominique Cahard, Delphine Dru, Tatiana Besset, Marie-Charlotte Belhomme, Thomas Poisson, Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), and Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
chemistry.chemical_classification, Glycal, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Copper mediated, chemistry.chemical_element, [CHIM.CATA]Chemical Sciences/Catalysis, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 010402 general chemistry, 01 natural sciences, Copper, Combinatorial chemistry, Catalysis, 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, Direct route, chemistry, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Fluorine, Surface modification, ComputingMilieux_MISCELLANEOUS, [CHIM.CHEM]Chemical Sciences/Cheminformatics
Abstract

A copper-mediated fluorofunctionalization of alkenes and alkynes has been developed. This method provides ready access to trisubstituted difluoromethylated olefins (from dihydropyrans, glycal derivatives, or terminal alkynes) or to tetrasubstituted olefins (from disubstituted alkynes). The products were obtained in good to high yields with acceptable E/Z selectivities. Finally, a first direct route to difluoromethylated alkynes is reported, albeit with low yields.

Published
2014

21. Copper-catalyzed olefinic C–H difluoroacetylation of enamides

Author

Laurence Grimaud, Xavier Pannecoucke, Marie-Charlotte Belhomme, Gilles Caillot, Jeremy Dufour, Isabelle Gillaizeau, Thomas Poisson, Institut de Chimie Organique et Analytique (ICOA), Université d'Orléans (UO)-Centre National de la Recherche Scientifique (CNRS)-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Institut de Chimie du CNRS (INC)-Institut National de la Santé et de la Recherche Médicale (INSERM), Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Rouen Normandie (UNIROUEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS), Processus d'Activation Sélective par Transfert d'Energie Uni-électronique ou Radiatif (UMR 8640) (PASTEUR), Université Pierre et Marie Curie - Paris 6 (UPMC)-Département de Chimie - ENS Paris, École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université d'Orléans (UO)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), École normale supérieure - Paris (ENS-PSL), and Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-École normale supérieure - Paris (ENS-PSL)

Subjects
Stereochemistry, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 010402 general chemistry, 01 natural sciences, Catalysis, [CHIM.ANAL]Chemical Sciences/Analytical chemistry, Materials Chemistry, ComputingMilieux_MISCELLANEOUS, 010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Metals and Alloys, Late stage, Substrate (chemistry), Regioselectivity, General Chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, Combinatorial chemistry, 0104 chemical sciences, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, Ceramics and Composites, Copper catalyzed, Surface modification, [CHIM.CHEM]Chemical Sciences/Cheminformatics
Abstract

Copper-catalyzed olefinic difluoroacetylation of enamides via direct C–H bond functionalization using BrCF2CO2Et is reported for the first time. It constitutes an efficient radical-free method for the regioselective synthesis of β-difluoroester substituted enamides which exhibits broad substrate scope, and thus demonstrates its potent application in a late stage fluorination strategy.

Published
2014

22. ChemInform Abstract: Copper Catalyzed β-Difluoroacetylation of Dihydropyrans and Glycals by Means of Direct C-H Functionalization

Author

Xavier Pannecoucke, Marie-Charlotte Belhomme, and Thomas Poisson

Subjects
chemistry.chemical_classification, Chemistry, Copper catalyzed, Surface modification, Glycoside, chemistry.chemical_element, Single step, General Medicine, Combinatorial chemistry, Copper, Catalysis
Abstract

A copper catalyzed direct functionalization of dihydropyrans and glycals has been developed. This method affords a new and straightforward access to C-2-CF2 dihydropyrans and glycosides in a single step starting from readily available starting materials. This new copper based catalytic system, probably involving a Cu(III) species as supported by experiments, allows the formation of the valuable fluorinated glycosides in good yields.

Published
2013

23. Copper catalyzed β-difluoroacetylation of dihydropyrans and glycals by means of direct C-H functionalization

Author

Thomas Poisson, Marie-Charlotte Belhomme, Xavier Pannecoucke, Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Institut Normand de Chimie Moléculaire Médicinale et Macromoléculaire (INC3M), Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Université Le Havre Normandie (ULH), Normandie Université (NU)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Université de Caen Normandie (UNICAEN), Normandie Université (NU)-Institut de Chimie du CNRS (INC)-École Nationale Supérieure d'Ingénieurs de Caen (ENSICAEN), Normandie Université (NU)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), and Institut National des Sciences Appliquées (INSA)-Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Hydrocarbons, Fluorinated, chemistry.chemical_element, Single step, 010402 general chemistry, 01 natural sciences, Biochemistry, Catalysis, Molecule, Organic chemistry, Glycosides, Physical and Theoretical Chemistry, Pyrans, chemistry.chemical_classification, Molecular Structure, 010405 organic chemistry, Hydrogen bond, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Glycoside, Hydrogen Bonding, Copper, 0104 chemical sciences, chemistry, Copper catalyzed, Surface modification
Abstract

International audience; A copper catalyzed direct functionalization of dihydropyrans and glycals has been developed. This method affords a new and straightforward access to C-2-CF2 dihydropyrans and glycosides in a single step starting from readily available starting materials. This new copper based catalytic system, probably involving a Cu(III) species as supported by experiments, allows the formation of the valuable fluorinated glycosides in good yields.

Published
2013

24. ChemInform Abstract: Copper-Catalyzed Direct Arylation of Cyclic Enamides Using Diaryliodonium Salts

Author

Xavier Pannecoucke, Thomas Poisson, Laetitia Chausset‐Boissarie, Marie-Charlotte Belhomme, Isabelle Gillaizeau, and Nicolas Gigant

Subjects
chemistry.chemical_compound, chemistry, Functional group, Copper catalyzed, Regioselectivity, chemistry.chemical_element, General Medicine, Combinatorial chemistry, Copper
Abstract

A convenient method for the copper(II)-catalyzed direct arylation of cyclic and nonaromatic enamides using diaryliodonium salts has been developed. The reaction demonstrates large functional group tolerance, good yields, and total regioselectivity with a C(3)-functionalization. The synthetic potential of this coupling was explored by using a range of readily accessible diaryliodonium salts and enamides.

Published
2013

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