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31 results on '"Anthore‐Dalion, Lucile"'

3. A Copper(I)‐Catalyzed Sulfonylative Hiyama Cross‐Coupling

Author

Adenot, Aurélien, Anthore-Dalion, Lucile, Nicolas, Emmanuel, Berthet, Jean-Claude, Thuéry, Pierre, Cantat, Thibault, Berthet, Jean‐claude, Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF) (LCMCE), Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M) (NIMBE UMR 3685), Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), GENCI for computing time (Allocation n°A0100806494), Institut de France, European Project: ERC CoG n°818260 ,ReNewHydrides, Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut Rayonnement Matière de Saclay (IRAMIS), and Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
High energy, Reaction mechanism, chemistry.chemical_element, 010402 general chemistry, 01 natural sciences, Reductive elimination, Catalysis, chemistry.chemical_compound, Polymer chemistry, Molecule, Coupling, Silanes, 010405 organic chemistry, Aryl, Organic Chemistry, Esters, [CHIM.CATA]Chemical Sciences/Catalysis, General Chemistry, Ketones, Copper, 0104 chemical sciences, Coupling (electronics), chemistry
Abstract

International audience; An air-tolerant Cu-catalyzed sulfonylative Hiyama cross-coupling reaction enabling the formation of diaryl sulfones is described. Starting from aryl silanes, DABSO and aryliodides, the reaction tolerates a large variety of polar functional groups (amines, ketones, esters, aldehydes). Control experiments coupled with DFT calculations shed light on the mechanism, characterized by the formation of a Cu(I)-sulfinate intermediate via fast insertion of a SO$_2$ molecule.

Published
2021

6. Organocatalysts confined within the cavity of cyclodextrins

Author

Bijouard, Kajetan, Maruchenko, Régina, Anthore-Dalion, Lucile, Sollogoub, Matthieu, Cantat, Thibault, Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF) (LCMCE), Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M) (NIMBE UMR 3685), Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), École normale supérieure - Paris (ENS-PSL), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-École normale supérieure - Paris (ENS-PSL), and Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[CHIM.CATA]Chemical Sciences/Catalysis
Abstract

International audience

Published
2022

8. Alkyl formates as transfer hydroalkylation reagents -Hydrobenzylation of imines

Author

Crochet, Etienne, Anthore-Dalion, Lucile, Cantat, Thibault, Palacin, Serge, Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF) (LCMCE), Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M) (NIMBE UMR 3685), Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Rayonnement Matière de Saclay (IRAMIS), and Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
[CHIM.ORGA]Chemical Sciences/Organic chemistry, [CHIM.ORGA] Chemical Sciences/Organic chemistry
Abstract

International audience; Hydrofunctionalization of unsaturated bonds, such as carbonyl, imines, alkenes or alkynes, provide a rapid and atom-economic access to functionalized molecules. Among those processes, hydroalkylation, which formally adds a R-H alkane across a C=C, C=O or C=N bond, has been intensively studied. However, in these reactions a sacrificial hydride or hydrogen donor is required, usually a hydrosilane or a hydroborane. Therefore, hydroalkylation by transfer was explored to increase the atom economy. In 2011, Oshima's group proposed a transfer from allenyl or homoallyl alcohols to aldehydes or imines under Cu-catalysis. Then, in 2013, Tang's group designed efficient and versatile hydroalkyl-donors based on Hantzsch esters or benzothiazoles. Yet, these two reactions did not improved the atom economy, although recyclable but under harsh conditions. Following previous work on transfer hydrosilylation, formate appeared as a new potential transfer reagent. We assumed that alkyl formates can perform transfer hydroalkylation reactions through transition-metal catalysis. This process would present a high atom economy and CO$_2$, as the only byproduct, can be recycle in formic acid, which can also be biosourced. As a proof of concept, we developed a novel catalytic reaction of transfer hydroalkylation from alkyl formates using benzyl formates and imines as model reagents.

Published
2022

9. Alkyl Formates as Transfer Hydroalkylation Reagents and Their Use in the Catalytic Conversion of Imines to Alkylamines**.

Author

Crochet, Etienne, Anthore‐Dalion, Lucile, and Cantat, Thibault

Subjects
*FORMATES, *IMINES, *RUTHENIUM catalysts, *FORMIC acid, *ESTERIFICATION, *TERTIARY amines
Abstract

Easily accessible via a simple esterification of alcohols with formic acid, alkyl formates are used as a novel class of transfer hydroalkylation reagents, CO2 acting as a traceless linker. As a proof‐of‐concept, their reactivity in the transfer hydroalkylation of imines is investigated, using a ruthenium‐based catalyst and LiI as promoter to cleave the C−O σ‐bond of the formate scaffold. Providing tertiary amines, the reaction displays a divergent regioselectivity compared to previously reported transfer hydroalkylation strategies. [ABSTRACT FROM AUTHOR]

Published
2023
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12. Silyl formates as hydrosilane surrogates for the transfer hydrosilylation of ketones.

Author

Romero, R. Martin, Thyagarajan, Neethu, Hellou, Nora, Chauvier, Clément, Godou, Timothé, Anthore-Dalion, Lucile, and Cantat, Thibault

Subjects
FORMATES, HYDROSILYLATION, RUTHENIUM catalysts, KETONES, SILYL ethers
Abstract

A transfer hydrosilylation of ketones employing silyl formates as hydrosilane surrogates under mild conditions is presented. A total of 24 examples of ketones have been successfully converted to their corresponding silyl ethers with 61–99% yields in the presence of a PNHP-based ruthenium catalyst and silyl formate reagent. The crucial role of the ligand for the transformation is demonstrated. [ABSTRACT FROM AUTHOR]

Published
2022
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13. Catalytic Reduction and Conversion of Small Molecules (CO2, SO2, N2O)

Author

Anthore-Dalion, Lucile, Cantat, Thibault, Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF) (LCMCE), Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M) (NIMBE UMR 3685), Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut Rayonnement Matière de Saclay (IRAMIS), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Palacin, Serge, Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Institut Rayonnement Matière de Saclay (IRAMIS), and Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)

Subjects
[CHIM.CATA] Chemical Sciences/Catalysis, [CHIM.COOR]Chemical Sciences/Coordination chemistry, [CHIM.CATA]Chemical Sciences/Catalysis, [CHIM.COOR] Chemical Sciences/Coordination chemistry
Abstract

International audience; Most of our chemical commodities relies on non-renewable resources and in particular on the oxidation of hydrocarbons. The need to find novel and renewable feedstocks for the production of both bulk and fine chemicals have led the chemical community to consider starting materials of high oxidation states such as CO2 or biomass. In this context, reductive strategies to convert these in valuable chemicals have emerged. Over the last years, our group has intensively worked on the development of catalytic systems to reduce CO and C=O bonds, allowing the reductive functionalization of CO2 in a so-called diagonal approach, 1 as well as the recycling of oxygenated polymers. 2 Thus, reactions involving mild reducing agents such as silanes or boranes in presence of organo-or organometallic catalysts have been developed. 3 Recent extensions of this methodology also enabled the reduction of other oxygenated compounds, with the direct synthesis of sulfones from SO2 4 and the reduction of N2O.

Published
2019

20. A Radical Approach to the Alkylation of Ketones

Author

Anthore-Dalion, Lucile, STAR, ABES, Laboratoire de synthèse organique (DCSO), École polytechnique (X)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Paris Saclay (COmUE), and Samir Z. Zard

Subjects
Radical Chemistry, Synthesis, Cétones, Alkylation, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Xanthate chemistry, Synthèse, Chimie des xanthates, Chimie radicalaire, Ketones, [CHIM.ORGA] Chemical Sciences/Organic chemistry
Abstract

This manuscript is dedicated to the development of new reactions based on xanthate radical transfer reaction, which has been developed in our laboratory. In particular, we were particularly interested in its application to the formal alkylation of ketones. Within this project, we studied a bidirectional alkylation of non-symmetrical ketones from dixanthates derivatives. Based on the difference of stability of the radicals involved in the reaction, this strategy allowed the preparation of various formally dialkylated ketones from unactivated alkenes. This powerful strategy was also applied to the formal alkylation of the highly base˗sensitive gem˗α˗dichloroketones. The mild and neutral conditions employed for the radical addition allowed the preparation of various derivatives. Their reactivities towards a Favorskii rearrangement were as well studied. The scope of a radical vinylation reaction was also extended to the synthesis of various trifluoromethylated ketones and enones. Finally, the development of new reactions from the radical adduct was envisaged., Cette thèse décrit le développement de nouvelles réactions dans le cadre de la chimie radicalaire par transfert de xanthate développée au laboratoire. Nous nous sommes tout particulièrement intéressés à apporter des solutions à l’alkylation formelle de cétones par voie radicalaire. Dans ce cadre, une alkylation bidirectionnelle de cétones non symétriques a été développée à partir de dixanthates. Reposant sur les différences de stabilité des radicaux présents dans le milieu, cette réaction a permis la synthèse de nombreuses cétones formellement dialkylées à partir d’oléfines non activées. La puissance de cette technologie a également été éprouvée dans le cadre de l’alkylation formelle des gem˗α˗dichlorocétones, composés très sensibles aux conditions basiques. Les conditions douces et neutres de réaction ont permis de préparer de nombreux dérivés et d’étudier plus en détails leur réactivité vis-à-vis du réarrangement de Favorskii. Dans un troisième temps, une réaction de vinylation radicalaire a été appliquée à la synthèse de cétones trifluorométhylées. Enfin, le développement de nouvelles réactions à partir des adduits radicalaires est envisagé.

Published
2016

24. SO2 conversion to sulfones: development and mechanistic insights of a sulfonylative Hiyama cross-coupling.

Author

Adenot, Aurélien, Char, Joëlle, von Wolff, Niklas, Lefεave;vre, Guillaume, Anthore-Dalion, Lucile, and Cantat, Thibault

Subjects
SULFONES, FUNCTIONAL groups, INSIGHT, ANIONS
Abstract

A Pd-catalyzed Hiyama cross-coupling reaction using SO2 is described. The use of silicon-based nucleophiles leads to the formation of allyl sulfones under mild conditions with a broad functional group tolerance. Control experiments coupled with DFT calculations shed light on the key steps of the reaction mechanism, revealing the crucial role of a transient sulfinate anion. [ABSTRACT FROM AUTHOR]

Published
2019
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26. Synthesis of Polyfunctionalized Triaryllanthanum Reagents by Using Ph3La and Related Species as Exchange Reagents.

Author

Benischke, Andreas D., Anthore‐Dalion, Lucile, Kohl, Fabien, and Knochel, Paul

Subjects
*LANTHANUM compounds, *ISOQUINOLINE, *FUNCTIONAL groups, *ALDEHYDES, *ELECTROPHILES, *REACTIVITY (Chemistry)
Abstract

Abstract: Ph3La⋅5 LiCl and the related (m‐xylyl)3La⋅5 LiCl were used as Hal/La exchange reagents (Hal=Br, I) for the preparation of various triaryl‐ and triheteroaryl‐lanthanum derivatives. These new exchange reagents are compatible with isoquinolines and some functional groups such as a nitrile or an ester. The reactivity of the resulting lanthanum compounds towards electrophiles, such as ketones, aldehydes, N,N‐dimethylamides, and primary alkyl halides was investigated. Additionally, a Pd‐catalyzed cross‐coupling procedure with aryl bromides was developed. [ABSTRACT FROM AUTHOR]

Published
2018
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27. A Copper(I)-Catalyzed Sulfonylative Hiyama Cross-Coupling.

Author

Adenot A, Anthore-Dalion L, Nicolas E, Berthet JC, Thuéry P, and Cantat T

Subjects
Catalysis, Esters, Ketones, Copper, Silanes
Abstract

An air-tolerant Cu-catalyzed sulfonylative Hiyama cross-coupling reaction enabling the formation of diaryl sulfones is described. Starting from aryl silanes, DABSO and aryliodides, the reaction tolerates a large variety of polar functional groups (amines, ketones, esters, aldehydes). Control experiments coupled with DFT calculations shed light on the mechanism, characterized by the formation of a Cu(I)-sulfinate intermediate via fast insertion of a SO 2 molecule., (© 2021 Wiley-VCH GmbH.)

Published
2021
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28. SO 2 conversion to sulfones: development and mechanistic insights of a sulfonylative Hiyama cross-coupling.

Author

Adenot A, Char J, von Wolff N, Lefèvre G, Anthore-Dalion L, and Cantat T

Abstract

A Pd-catalyzed Hiyama cross-coupling reaction using SO2 is described. The use of silicon-based nucleophiles leads to the formation of allyl sulfones under mild conditions with a broad functional group tolerance. Control experiments coupled with DFT calculations shed light on the key steps of the reaction mechanism, revealing the crucial role of a transient sulfinate anion.

Published
2019
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29. The Halogen-Samarium Exchange Reaction: Synthetic Applications and Kinetics.

Author

Anthore-Dalion L, Benischke AD, Wei B, Berionni G, and Knochel P

Abstract

Fast I/Sm and Br/Sm exchanges take place when various aromatic or heterocyclic iodides and bromides are treated with nBu 2 SmCl⋅4 LiCl and nBu 3 Sm⋅5 LiCl, respectively. The resulting organosamarium reagents were efficiently quenched with aldehydes, ketones, and imines. Also, they undergo acylations when treated with N,N-dimethylamides leading to ketones. The rate of the Br/Sm exchange for a typical aryl bromide was determined and found to be 8.5×10 5 faster than the Br/Mg exchange, indicating that the rate of a metal-exchange is related to the ionic character of the carbon-metal bond and to the metal electronegativity., (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2019
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30. Synthesis of Polyfunctionalized Triaryllanthanum Reagents by Using Ph 3 La and Related Species as Exchange Reagents.

Author

Benischke AD, Anthore-Dalion L, Kohl F, and Knochel P

Abstract

Ph 3 La⋅5 LiCl and the related (m-xylyl) 3 La⋅5 LiCl were used as Hal/La exchange reagents (Hal=Br, I) for the preparation of various triaryl- and triheteroaryl-lanthanum derivatives. These new exchange reagents are compatible with isoquinolines and some functional groups such as a nitrile or an ester. The reactivity of the resulting lanthanum compounds towards electrophiles, such as ketones, aldehydes, N,N-dimethylamides, and primary alkyl halides was investigated. Additionally, a Pd-catalyzed cross-coupling procedure with aryl bromides was developed., (© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2018
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31. Preparation of Functionalized Diaryl- and Diheteroaryllanthanum Reagents by Fast Halogen-Lanthanum Exchange.

Author

Benischke AD, Anthore-Dalion L, Berionni G, and Knochel P

Abstract

Aryl and heteroaryl halides (X=Br, I) undergo a fast and convenient halogen-lanthanum exchange with nBu 2 LaMe, which leads to functionalized diaryl- and diheteroaryllanthanum derivatives. Subsequent trapping reactions with selected electrophiles, such as ketones, aldehydes, or amides, proceeded smoothly at -50 °C in THF, affording polyfunctionalized alcohols and carbonyl derivatives. Kinetic competition experiments revealed a similar reactivity trend as for Br/Mg exchange, but 10 6 -times higher rates, making it comparable to Br/Li exchange., (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2017
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