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2. Gold-Catalyzed Domino Reactions

Author

Michelet, Véronique, Bayley, Hagan, Series editor, Houk, Kendall N., Series editor, Hughes, Greg, Series editor, Hunter, Christopher A., Series editor, Ishihara, Kazuaki, Series editor, Krische, Michael J, Series editor, Lehn, J.-M., Series editor, Luque, Rafael, Series editor, Olivucci, Massimo, Series editor, Siegel, Jay S., Series editor, Thiem, Joachim, Series editor, Venturi, Margherita, Series editor, Wong, Chi-Huey, Series editor, Wong, Henry N.C., Series editor, and Slaughter, LeGrande M., editor

Published
2015
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7. Chiral 1,4-Oxazino[4,3- a ]indoles as a Challenging Scaffold: Syntheses and Properties.

Author

Dupeux, Aurélien and Michelet, Veronique

Subjects
*INDOLE compounds, *MORPHOLINE, *ANTINEOPLASTIC agents, *ASYMMETRIC synthesis, *INDOLE, *SPINE
Abstract

In the last few decades, there has been an increasing interest in the development of new syntheses of oxazinoindoles, a tricyclic backbone bearing an indole core structure fused with a morpholine ring, in particular because these molecules have interesting bioactive properties, such as antidepressant, anti-inflammatory, or antitumor activity. There are a few reported racemic strategies for the synthesis of oxazinoindoles, but only four reports of enantioselective syntheses. This short review presents an overview of these enantioselective strategies as well as the evaluation of chiral oxazinoindoles for their bioactive properties. 1 Introduction 2 Racemic Syntheses and Evaluation of Chiral Oxazinoindoles after Separation 3 Enantioselective Catalytic Syntheses of Oxazinoindoles 4 Conclusion [ABSTRACT FROM AUTHOR]

Published
2023
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17. Selective Metals Determination with a Photoreversible Spirobenzopyran

Author

Evans, Lawrence, III, Collins, Greg E., Shaffer, Ronald E., Michelet, Veronique, and Winkler, Jeffrey D.

Subjects
Chemical detectors -- Research, Metals -- Analysis, Water -- Contamination, Chemistry
Abstract

The photoreversible metal-ion complexation behavior of nitroquinolinospiropyranindoline (NQSP) was studied in combination with the selective identification of six different transition-metal ions, Zn(super 2+), Co(super 2+), Hg(super 2+), Cu(super 2+), Cd(super 2+), and Ni(super 2+), in single- and binary-component mixtures via partial least squares discriminant (PLSD) analysis. The plasticizer, dicapryl phthalate, was chosen as the support medium for this study on the basis of (1) its enhancement of the photoreversibility and hypsochromic shifts seen in metal complexation and (2) its potential application to supported liquid membranes for eventual sensor applications. Complexation of divalent transition-metal ions by NQSP in dicapryl phthalate produced variable hypsochromic shifts in the absorption spectra (30-60 nm), requiring chemometric techniques in order to overcome the spectral overlaps. PLSD analysis was used to build classification analysis models to differentiate between the six divalent transition-metal ions. The feasibility of performing mixture analysis was studied using the concept of net analyte signal prior to experimental verification. Single- and binary-component mixtures of metals were identified with 100 and 97.4% accuracy, respectively, which included no false positives in either the training or prediction sets.

Published
1999

18. Photodynamic fluorescent metal ion sensors with parts per billion sensitivity

Author

Winkler, Jeffrey D., Bowen, Corinne M., and Michelet, Veronique

Subjects
Metal ions -- Research, Sensors -- Research, Chemistry
Abstract

The synthesis and spectroscopic analysis of the first highly fluorescent photoreversible spiropyrandinolines as metal ion sensors with greater sensitivity and lower fatigue rates are reported. Results establish that fluorescence spectroscopy can be used to detect chemically and photochemically reversible metal ion binding, with sensitivity for Zn(super 2+) in the parts per billion range. This novel photodynamic sensing material can be attached to fiber optic surfaces for the development of a metal-ion sensing device.

Published
1998

21. Bimetallic Oriented (Au/Cu2O) vs. Monometallic 1.1.1 Au (0) or 2.0.0 Cu2O Graphene-Supported Nanoplatelets as Very Efficient Catalysts for Michael and Henry Additions

Author

Simion, Andrada, Candu, Natalia, Coman, Simona M., Primo Arnau, Ana Maria, Esteve-Adell, Iván, Michelet, Veronique, Parvulescu, Vasile I., and García Gómez, Hermenegildo

Subjects
QUIMICA ORGANICA, Heterogeneous catalysts, Nanoplatelets, Gold, Graphene, Copper
Abstract

[EN] Michael and Henry addition reactions have been investigated using mono (Au and Cu2O) and bimetallic nanoplatelets (Au/Cu2O) grafted onto few-layers graphene (fl-G) films as heterogeneous catalysts by comparison with homogeneous NaOH and K2CO3 ones. In the presence of the heterogeneous catalysts, these reactions occurred in the absence of any extrinsic (NaOH and K2CO3) base with turnover numbers (TONs) at least four orders of magnitude higher. While the homogeneous catalysts provided TONs close to the unity for Au/Cu2O/fl-G this was of the order of 10(7). These reactions also occurred with a very good selectivity to the targeted products. These performances are in line with the basicity of these catalysts demonstrated from CO2 chemisorption measurements. The effect of the nanosize and the interaction of the nanoparticles with the graphene are also important to achieve this high activity., This work was supported by the Ministere de l' Education, de la Recherche et des Affaires Etrangeres (Brancusi Program) of France (PN-III-CEI-BIM-PM, nr. 80BM/2017), UEFISCDI (PN-III-P4-ID-PCE-2016-0146, nr. 121/2017) and COST Action CA15106 (CHAOS)

Published
2018

24. In[Cl.sub.3]/CyN[H.sub.2] cocatalyzed carbocyclization reaction: an entry to [alpha]-disubstituted exo-methylene cyclopentanes

Author

Montaignac, Benjamin, Vitale, Maxime R., Ratovelomanana-Vidal, Virginie, and Michelet, Veronique

Subjects
Amines -- Chemical properties, Carbenes -- Structure, Carbenes -- Chemical properties, Indium -- Chemical properties, Substitution reactions -- Analysis, Biological sciences, Chemistry
Abstract

An efficient and cost-effective synthetic approach to functionalized exo-methylene cyclopentanes developed from [alpha]-disubstituted formyl-alkynes by merging amine catalysis with the indium activation of alkynes is described. The mechanistic study provides insight into the critical role of the amine cocatalyst and the development of a new cooperative catalytic system which permitted the cyclization of a broad range of substrates.

Published
2010

25. Pt[Cl.sub.2]-catalyzed cycloisomerization of 1,6-enynes for the synthesis of substituted bicyclo[3.1.0]hexanes

Author

Liu Ye, Qian Chen, Jiancun Zhang, and Michelet, Veronique

Subjects
Acetaldehyde -- Chemical properties, Acetaldehyde -- Structure, Hexane -- Chemical properties, Hexane -- Structure, Isomerization -- Usage, Platinum compounds -- Chemical properties, Platinum compounds -- Structure, Biological sciences, Chemistry
Abstract

The mild and efficient Pt[Cl.sub.2]-catalyzed cycloisomerization of 1,6-enynes containing a heteroatom substituent at the propargylic position is described. The reactions is able to produce 1-alkenylbicyclo[3.1.0]hexanes in good to excellent yields or 2-(bicyclo[3.1.0]hex-1-yl)acetaldehydes in moderate yields.

Published
2009

26. Room temperature Au(I)-catalyzed exo-selective cycloisomerization of acetylenic acids: An entry to functionalized gamma-lactones

Author

Genin, Emilie, Toullec, Patrick Yves, Antoniotti, Sylvain, Brancour, Celia, Genet, Jean-Pierre, and Michelet, Veronique

Subjects
Gold compounds -- Chemical properties, Lactones -- Chemical properties, Catalysts -- Chemical properties, Chemistry
Abstract

The first gold-catalyzed cyclization of acetylenic acids at room temperature leading to functionalized lactones is reported. Results demonstrates that functionalized acetylenic acids might be cyclized under extremely mild conditions, at room temperature in the presence of AuCl catalyst, and without additives.

Published
2006

27. Highly efficient access to strained bicyclic ketals via gold-catalyzed cycloisomerization of bis-homopropargylic diols

Author

Antoniotti, Sylvain, Genin, Emilie, Michelet, Veronique, and Genet, Jean-Pierre

Subjects
Glycols -- Structure, Glycols -- Chemical properties, Ring formation (Chemistry) -- Analysis, Isomerization -- Analysis, Chemistry
Abstract

The preliminary results concerning a general room temperature Au(super I)- and Au(super III)- catalyzed cycloisomerization of bis-homopropargylic diols leading to strained dioxabicyclo ketals are described. Either Au(super I) or Au(super III) catalysts promote a highly efficient cycloisomerization of bis-homopropargylic diols under very mild conditions and in very short time.

Published
2005

36. Chapitre 12 : Architectures moléculaires : synthèses, mécanismes et propriétés

Author

Andraud, Chantal, Ardisson, Janick, Bourissou, Didier, Dunach, Elisabet, Guillemin, J.C., Jauffret, Philippe, Kahn, Philippe, Legoupy, Stéphanie, Legros, Julien, Lesot, Philippe, Maddaluno, Jacques, Maggiani, A., Martinez, Jean, Michelet, Veronique, Sallé, Marc, Laboratoire de Chimie - UMR5182 (LC), École normale supérieure - Lyon (ENS Lyon)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Centre National de la Recherche Scientifique (CNRS), Chimie Organique, Médicinale et Extractive et Toxicologie Expérimentale (COMETE - UMR 8638), Université Paris Descartes - Paris 5 (UPD5)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA), Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie de Toulouse (ICT-FR 2599), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie des Molécules bioactives et des aromes (cnrs, umr 6001), Université Nice Sophia Antipolis (... - 2019) (UNS), Université Côte d'Azur (UCA)-Université Côte d'Azur (UCA), Institut des Sciences Chimiques de Rennes (ISCR), Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Rennes-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES), SOCIÉTÉ ISIS FORMATION, Unité de chimie organique moléculaire et macromoléculaire (UCO2M), Le Mans Université (UM)-Centre National de la Recherche Scientifique (CNRS), Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Centre National de la Recherche Scientifique (CNRS)-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), Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS), Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS), Centre Interdisciplinaire de Nanoscience de Marseille (CINaM), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Charles Friedel, Université Pierre et Marie Curie - Paris 6 (UPMC)-Ecole Nationale Supérieure de Chimie de Paris- Chimie ParisTech-PSL (ENSCP)-Centre National de la Recherche Scientifique (CNRS), MOLTECH-ANJOU (MOLTECH-ANJOU), Centre National de la Recherche Scientifique (CNRS)-Université d'Angers (UA), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes-Centre National de la Recherche Scientifique (CNRS)

Subjects
[CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS
Abstract

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Published
2011

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