Stéphane Menuel

Université d'Artois

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ÉM

Éric Monflier

Centre National de la Recherche Scientifique

Frédéric Hapiot

Université d'Artois

Sébastien Tilloy

Unité de catalyse et de chimie du solide de Lille

Hervé Bricout

Université d'Artois

Jonathan Potier

Unité Matériaux et Transformations

Anne Ponchel

Université de Lille

Patrice Woisel

Unité Matériaux et Transformations

Alain Marsura

Centre National de la Recherche Scientifique

Jolanta Rousseau

Université d'Artois

Bastien Léger

Université d'Artois

Cooperative Institutions

Centre National de la Recherche Scientifique

Université d'Artois

Université de Lille

Unité de catalyse et de chimie du solide de Lille

Catalyse

École Centrale de Lille

École Nationale Supérieure de Chimie de Lille

Université Lille Nord de France

Université de Lorraine

Institut de Recherche sur les Systèmes Atomiques et Moléculaires Complexes

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ChemInform Abstract: Greener Paal—Knorr Pyrrole Synthesis by Mechanical Activation.

ChemInform (2016)

Liudvikas Akelis Jolanta Rousseau Robertas Juškėnas Jelena Dodonova Cyril Rousseau

Abstract N‐substituted pyrroles are synthesized by the Paal—Knorr reaction using mechanical activation in a ball mill.

Pyrrole

10.1002/chin.201621150

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Synthesis and Complexation Ability of a Novel Bis- (guanidinium)-tetrakis-(β-cyclodextrin) Dendrimeric Tetrapod as a Potential Gene Delivery (DNA and siRNA) System. Study of Cellular siRNA Transfection

Bioconjugate Chemistry (2008)

Stéphane Menuel Stéphane Fontanay Igor Clarot Raphaël E. Duval Laurent Diez

The facile synthesis of a novel bis-(guanidinium)-tetrakis-(β-cyclodextrin) tetrapod, the first example of a new host family, was described, and the ability of the cyclodextrin CyD tetrapod to form molecular association with siRNA and DNA guest molecules was demonstrated. Affinity capillary electrophoresis was used to determine the binding constant with the evaluation of the shift in the electrophoretic mobility μ of injected siRNA when various CyD tetrapod concentrations were added to the run buffer. A significant association constant (Ka =16 000 M−1) was obtained with borate buffer when double-stranded siRNA was primarily opened with the help of temperature. An efficient cellular transfection of siRNA into human embryonic lung fibroblasts was observed by fluorescence microscopy.

Binding constant

Tetrapod (structure)

10.1021/bc800193p

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Citations (43)

New synthetic approach to per-O-acetyl-isocyanates, isothiocyanates and thioureas in the disaccharide and cyclodextrin series

New Journal of Chemistry (2006)

Stéphane Menuel Stanisław Porwański Alain Marsura

An efficient method for the preparation of per-O-acetyl disaccharides and cyclodextrin isocyanates or isothiocyanates by the phosphine imide strategy is reported. Successful one-pot, high yield syntheses of cellobiose, lactose and sucrose isocyanates or/and isothiocyanates pure β-anomers have been completed starting from their corresponding monoazido-per-O-acetyl derivatives. Transformation of the ACEtris-6-azido-per-O-methylated and the ACEtris-6-azido-per-O-acetylated-α-cyclodextrins or of the 6A-azido-6A-deoxy-per-O-acetyl-β-cyclodextrin into the corresponding isocyanates and/or isothiocyanates is also presented. Finally the conversion of the cyclodextrin isothiocyanates by nucleophilic addition of primary and secondary amines into a large panel of original thioureido-cyclodextrins derivatives is described.

Disaccharide

10.1039/b600023a

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Citations (16)

Cooperativity in Aqueous Organometallic Catalysis: Contribution of Cyclodextrin-Substituted Polymers

ACS Catalysis (2012)

Jonathan Potier Stéphane Menuel David Fournier Sophie Fourmentin Patrice Woisel

Cooperativity has been implicated to explain the catalytic performances of cyclodextrin-substituted polymers in aqueous rhodium-catalyzed hydroformylation of 1-hexadecene, thus opening the door to the transformation of very hydrophobic substrates in aqueous biphasic catalysis by supramolecular means.

Cooperativity

Supramolecular catalysis

Organometallic Chemistry

10.1021/cs300254t

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Citations (44)

Pillar[5]arenes as Supramolecular Hosts in Aqueous Biphasic Rhodium-Catalyzed Hydroformylation of Long Alkyl-chain Alkenes

HAL (Le Centre pour la Communication Scientifique Directe) (2018)

Missipssa Benatmane Kévin Cousin Nérimel Laggoune Stéphane Menuel Éric Monflier

Pillar

Source

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Access to Pyrrole Derivatives in Water with the Assistance of Methylated Cyclodextrins

European Journal of Organic Chemistry (2014)

Stéphane Menuel Jolanta Rousseau Cyril Rousseau Edita Vaičiūnaite Jelena Dodonova

Abstract A new and efficient catalytic protocol with which to synthesize N ‐substituted pyrrole derivatives from amines and 1,4‐diketones by Paal–Knorr condensation in aqueous medium has been developed by using partially methylated β‐cyclodextrins (RAME‐β‐CD). The modified cyclodextrins were used as mass transfer agents without catalyst for reactive ketones and with nitrophenol as catalyst for more hindered ketones.

Pyrrole

Aqueous medium

10.1002/ejoc.201402327

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Citations (18)

Cyclodextrin-grafted polymers functionalized with phosphanes: a new tool for aqueous organometallic catalysis

Beilstein Journal of Organic Chemistry (2014)

Jonathan Potier Stéphane Menuel David Mathiron Véronique Bonnet Frédéric Hapiot

New cyclodextrin (CD)-grafted polymers functionalized with water-soluble phosphanes were synthesized in three steps starting from polyNAS. Once characterized by NMR spectroscopy and size-exclusion chromatography, they were used as additives in Rh-catalyzed hydroformylation of 1-hexadecene. The combined supramolecular and coordinating properties of these polymers allowed increasing the catalytic activity of the reaction without affecting the selectivities.

Organometallic Chemistry

10.3762/bjoc.10.276

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Citations (11)

Cyclodextrin–phosphane possessing a guest-tunable conformation for aqueous rhodium-catalyzed hydroformylation

Chemical Communications (2011)

Diem Ngan Tran François‐Xavier Legrand Stéphane Menuel Hervé Bricout Sébastien Tilloy

The inclusion of a guest inside the cavity of a new water-soluble cyclodextrin-phosphane allows controlling the natural conformation of this ligand leading to an inversion of the regioselectivity during aqueous hydroformylation reaction.

10.1039/c1cc16326d

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Citations (46)

Catalysis in Cyclodextrin-Based Unconventional Reaction Media: Recent Developments and Future Opportunities

ACS Sustainable Chemistry & Engineering (2017)

Frédéric Hapiot Stéphane Menuel Michel Ferreira Bastien Léger Hervé Bricout

During these last years, cyclodextrins (CDs) have greatly contributed to the development of innovative homogeneous or heterogeneous catalytic processes. More than simple molecular platforms aiming at designing new ligands or interfacial additives, CDs have been employed to generate unconventional reaction media such as supramolecular hydrogels or low melting mixtures (LMMs) capable of stabilizing active catalytic species. By using such alternative and unconventional media, high catalytic activities and selectivities were obtained in various transition metal catalytic reactions. The studied catalytic systems are easy to implement and allow for the remarkable stabilization of organometallic or metal nanoparticle catalysts. Interestingly, the size of metal nanoparticles can be finely tuned through confinement in the network of CD-based supramolecular hydrogels. Additionally, the catalysts can be recovered by a simple phase separation. The catalytic phase can be stored at room temperature under an air atmosphere in the solid state and reused as needed without significant loss of activity. Eventually, such CD-based catalytic systems greatly improve process safety. The present article intends to show the reader the very substantial progress that has recently been made in the field.

10.1021/acssuschemeng.6b02886

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Citations (54)

List of Contributors

Elsevier eBooks (2016)

Nicolas P. E. Barry Stefano Bellucci Giuseppe Borsato Kyu Bum Han F.G. Cirujano

10.1016/b978-0-12-801713-5.00019-7

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