0000000000300079
AUTHOR
Nejib Dwadnia
Hybrid ferrocene ligands (P, N) : synthesis, coordination to metals and applications in arylation coupling catalysis
The research theme developed during this thesis concerns the development of new hybrid ferrocene hybrid (P, N) ligands with controlled conformation, robust and stable to air. These hybrid tetradent ligands comprise two types of coordinating functions with distinct steric and electronic properties. Their coordination chemistry with metals such as gold or palladium has been studied and some isolated Au (I) complexes have been used in the arylation coupling catalysis of aryl iodides.
Highly Functionalized Ferrocenes
International audience; Ferrocene is unique among organometallic compounds, and serves notably as a versatile platform towards the production of ligands useful to promote transition metals chemistry. A general limiting aspect of the synthesis of ferrocene derivatives is the efficient access to sophisticated highly functionalized polysubstituted ferrocenes, i. e. bearing four or more substituents replacing hydrogen atoms on the cyclopentadienyl rings. These ferrocene derivatives can bear various functional or/and structuring spectator substituents. Their preparation involves synthetic difficulties resulting from the need of multiple functionalizations coexisting altogether, and satisfying fu…
Gold-Catalyzed Suzuki Coupling of ortho -Substituted Hindered Aryl Substrates
International audience; A method that allows hindered ortho-substituted aryl iodides to be efficiently coupled to phenylboronic acid using a gold-catalyzed C-C bond formation is presented. The use of a molecularly-defined dinuclear gold chloride catalytic precursor that is stabilized by a new tetradentate (N,N')-diamino-(P,P')-diphosphino ferrocene hybrid ligand in a Suzuki-type reaction is described for the first time. Electron-rich isopropyl groups on phosphorus were found essen-tial for a superior activity, while the performances of a set of analogous gold dinuclear complexes that were fully characterized by multinuclear NMR spectroscopy and XRD analysis, were investigated. Therefore, ar…
Aminomethyl-Substituted Ferrocenes and Derivatives: Straightforward Synthetic Routes, Structural Characterization, and Electrochemical Analysis
A variety of aminomethyl-substituted ferrocenes and the parent compounds (iminomethyl)ferrocenes, azaferrocenophanes, and diferrocenylamines can be selectively synthesized from reductive amination of 1,1′-diformylferrocene or formylferrocene. The optimized one- or two-step reactions have delivered 13 new compounds, isolated in 65–97% yields, which include tertiary (ferrocenylmethyl)amines and azaferrocenophanes by using NaBH(OAc)3 as a mild reducing agent and (iminomethyl)ferrocenes and secondary (ferrocenylmethyl)amines by using LiAlH4. X-ray structures of representative members of these ferrocene derivative families have evidenced the preferred conformation adopted by ferrocene backbones,…
Input of P, N-(phosphanyl, amino)-ferrocene hybrid derivatives in late transition metals catalysis
International audience; Unequally functionalized ferrocenes give access to valuable hemilabile reactivity in catalytic reaction. We address the synthesis of hybrid (P, N)-ferrocenyl compounds for which recent catalytic breakthrough applications have been reported, transversely in late transition metals chemistry. Palladium, nickel, rhodium, iridium, and emerging iron and gold catalysis are illustrated from selected examples, which include CC bond formation from cross-coupling and polymerization, allylic substitution, cyanation, hydroformylation, CH arylation and silylation and hydrogenation reactions.
Converging and Diverging Synthetic Strategies to Tetradentate (N,N′)-Diaminomethyl,(P,P′)-Ferrocenyl Ligands: Influence of tert-Butyl Groups on Ferrocene Backbone Conformation
Hexasubstituted hybrid tetradentate (N,N′,P,P′)-ferrocenes bearing phosphino and aminomethyl groups, plus hindering tert-butyl moieties, were synthesized by using two different strategies: a “diverging” synthesis involving successive functionalization of preformed di-tert-butylated ferrocene and a “converging” assembly of the species from appropriately substituted cyclopentadienyl rings. While the new cyclopentadienyl salts formed are of interest, their assembly with iron dichloride used as a “converging” way to produce tetradentate ferrocene ligands presented several drawbacks. Conversely, the synthesis of new tert-butylated (aminomethyl)ferrocene derivatives was found convenient to furthe…
CCDC 1433505: Experimental Crystal Structure Determination
Related Article: Fatima Allouch, Nejib Dwadnia, Nikolay V. Vologdin, Yurii V. Svyaschenko, Hélène Cattey, Marie-José Penouilh, Julien Roger, Daoud Naoufal, Ridha Ben Salem, Nadine Pirio, Jean-Cyrille Hierso|2015|Organometallics|34|5015|doi:10.1021/acs.organomet.5b00601
CCDC 1433497: Experimental Crystal Structure Determination
Related Article: Fatima Allouch, Nejib Dwadnia, Nikolay V. Vologdin, Yurii V. Svyaschenko, Hélène Cattey, Marie-José Penouilh, Julien Roger, Daoud Naoufal, Ridha Ben Salem, Nadine Pirio, Jean-Cyrille Hierso|2015|Organometallics|34|5015|doi:10.1021/acs.organomet.5b00601
CCDC 1433499: Experimental Crystal Structure Determination
Related Article: Fatima Allouch, Nejib Dwadnia, Nikolay V. Vologdin, Yurii V. Svyaschenko, Hélène Cattey, Marie-José Penouilh, Julien Roger, Daoud Naoufal, Ridha Ben Salem, Nadine Pirio, Jean-Cyrille Hierso|2015|Organometallics|34|5015|doi:10.1021/acs.organomet.5b00601
CCDC 1485963: Experimental Crystal Structure Determination
Related Article: Nejib Dwadnia, Julien Roger, Nadine Pirio, Hélène Cattey, Ridha Ben Salem, Jean-Cyrille Hierso|2017|Chem.Asian J.|12|459|doi:10.1002/asia.201601583
CCDC 980179: Experimental Crystal Structure Determination
Related Article: Nejib Dwadnia, Fatima Allouch, Nadine Pirio, Julien Roger, Hélène Cattey, Sophie Fournier, Marie-Josée Penouilh, Charles H. Devillers, Dominique Lucas, Daoud Naoufal, Ridha Ben Salem, and Jean-Cyrille Hierso|2013|Organometallics|32|5784|doi:10.1021/om400317s
CCDC 980175: Experimental Crystal Structure Determination
Related Article: Nejib Dwadnia, Fatima Allouch, Nadine Pirio, Julien Roger, Hélène Cattey, Sophie Fournier, Marie-Josée Penouilh, Charles H. Devillers, Dominique Lucas, Daoud Naoufal, Ridha Ben Salem, and Jean-Cyrille Hierso|2013|Organometallics|32|5784|doi:10.1021/om400317s
CCDC 1433506: Experimental Crystal Structure Determination
Related Article: Fatima Allouch, Nejib Dwadnia, Nikolay V. Vologdin, Yurii V. Svyaschenko, Hélène Cattey, Marie-José Penouilh, Julien Roger, Daoud Naoufal, Ridha Ben Salem, Nadine Pirio, Jean-Cyrille Hierso|2015|Organometallics|34|5015|doi:10.1021/acs.organomet.5b00601
CCDC 1433503: Experimental Crystal Structure Determination
Related Article: Fatima Allouch, Nejib Dwadnia, Nikolay V. Vologdin, Yurii V. Svyaschenko, Hélène Cattey, Marie-José Penouilh, Julien Roger, Daoud Naoufal, Ridha Ben Salem, Nadine Pirio, Jean-Cyrille Hierso|2015|Organometallics|34|5015|doi:10.1021/acs.organomet.5b00601
CCDC 1433501: Experimental Crystal Structure Determination
Related Article: Fatima Allouch, Nejib Dwadnia, Nikolay V. Vologdin, Yurii V. Svyaschenko, Hélène Cattey, Marie-José Penouilh, Julien Roger, Daoud Naoufal, Ridha Ben Salem, Nadine Pirio, Jean-Cyrille Hierso|2015|Organometallics|34|5015|doi:10.1021/acs.organomet.5b00601
CCDC 1433498: Experimental Crystal Structure Determination
Related Article: Fatima Allouch, Nejib Dwadnia, Nikolay V. Vologdin, Yurii V. Svyaschenko, Hélène Cattey, Marie-José Penouilh, Julien Roger, Daoud Naoufal, Ridha Ben Salem, Nadine Pirio, Jean-Cyrille Hierso|2015|Organometallics|34|5015|doi:10.1021/acs.organomet.5b00601
CCDC 1433504: Experimental Crystal Structure Determination
Related Article: Fatima Allouch, Nejib Dwadnia, Nikolay V. Vologdin, Yurii V. Svyaschenko, Hélène Cattey, Marie-José Penouilh, Julien Roger, Daoud Naoufal, Ridha Ben Salem, Nadine Pirio, Jean-Cyrille Hierso|2015|Organometallics|34|5015|doi:10.1021/acs.organomet.5b00601
CCDC 1485958: Experimental Crystal Structure Determination
Related Article: Nejib Dwadnia, Julien Roger, Nadine Pirio, Hélène Cattey, Ridha Ben Salem, Jean-Cyrille Hierso|2017|Chem.Asian J.|12|459|doi:10.1002/asia.201601583
CCDC 980177: Experimental Crystal Structure Determination
Related Article: Nejib Dwadnia, Fatima Allouch, Nadine Pirio, Julien Roger, Hélène Cattey, Sophie Fournier, Marie-Josée Penouilh, Charles H. Devillers, Dominique Lucas, Daoud Naoufal, Ridha Ben Salem, and Jean-Cyrille Hierso|2013|Organometallics|32|5784|doi:10.1021/om400317s
CCDC 980178: Experimental Crystal Structure Determination
Related Article: Nejib Dwadnia, Fatima Allouch, Nadine Pirio, Julien Roger, Hélène Cattey, Sophie Fournier, Marie-Josée Penouilh, Charles H. Devillers, Dominique Lucas, Daoud Naoufal, Ridha Ben Salem, and Jean-Cyrille Hierso|2013|Organometallics|32|5784|doi:10.1021/om400317s
CCDC 980174: Experimental Crystal Structure Determination
Related Article: Nejib Dwadnia, Fatima Allouch, Nadine Pirio, Julien Roger, Hélène Cattey, Sophie Fournier, Marie-Josée Penouilh, Charles H. Devillers, Dominique Lucas, Daoud Naoufal, Ridha Ben Salem, and Jean-Cyrille Hierso|2013|Organometallics|32|5784|doi:10.1021/om400317s
CCDC 980176: Experimental Crystal Structure Determination
Related Article: Nejib Dwadnia, Fatima Allouch, Nadine Pirio, Julien Roger, Hélène Cattey, Sophie Fournier, Marie-Josée Penouilh, Charles H. Devillers, Dominique Lucas, Daoud Naoufal, Ridha Ben Salem, and Jean-Cyrille Hierso|2013|Organometallics|32|5784|doi:10.1021/om400317s
CCDC 1433502: Experimental Crystal Structure Determination
Related Article: Fatima Allouch, Nejib Dwadnia, Nikolay V. Vologdin, Yurii V. Svyaschenko, Hélène Cattey, Marie-José Penouilh, Julien Roger, Daoud Naoufal, Ridha Ben Salem, Nadine Pirio, Jean-Cyrille Hierso|2015|Organometallics|34|5015|doi:10.1021/acs.organomet.5b00601
CCDC 1433500: Experimental Crystal Structure Determination
Related Article: Fatima Allouch, Nejib Dwadnia, Nikolay V. Vologdin, Yurii V. Svyaschenko, Hélène Cattey, Marie-José Penouilh, Julien Roger, Daoud Naoufal, Ridha Ben Salem, Nadine Pirio, Jean-Cyrille Hierso|2015|Organometallics|34|5015|doi:10.1021/acs.organomet.5b00601
CCDC 1433507: Experimental Crystal Structure Determination
Related Article: Fatima Allouch, Nejib Dwadnia, Nikolay V. Vologdin, Yurii V. Svyaschenko, Hélène Cattey, Marie-José Penouilh, Julien Roger, Daoud Naoufal, Ridha Ben Salem, Nadine Pirio, Jean-Cyrille Hierso|2015|Organometallics|34|5015|doi:10.1021/acs.organomet.5b00601
CCDC 1485961: Experimental Crystal Structure Determination
Related Article: Nejib Dwadnia, Julien Roger, Nadine Pirio, Hélène Cattey, Ridha Ben Salem, Jean-Cyrille Hierso|2017|Chem.Asian J.|12|459|doi:10.1002/asia.201601583
CCDC 980180: Experimental Crystal Structure Determination
Related Article: Nejib Dwadnia, Fatima Allouch, Nadine Pirio, Julien Roger, Hélène Cattey, Sophie Fournier, Marie-Josée Penouilh, Charles H. Devillers, Dominique Lucas, Daoud Naoufal, Ridha Ben Salem, and Jean-Cyrille Hierso|2013|Organometallics|32|5784|doi:10.1021/om400317s
CCDC 1485959: Experimental Crystal Structure Determination
Related Article: Nejib Dwadnia, Julien Roger, Nadine Pirio, Hélène Cattey, Ridha Ben Salem, Jean-Cyrille Hierso|2017|Chem.Asian J.|12|459|doi:10.1002/asia.201601583
CCDC 1485960: Experimental Crystal Structure Determination
Related Article: Nejib Dwadnia, Julien Roger, Nadine Pirio, Hélène Cattey, Ridha Ben Salem, Jean-Cyrille Hierso|2017|Chem.Asian J.|12|459|doi:10.1002/asia.201601583
CCDC 980181: Experimental Crystal Structure Determination
Related Article: Nejib Dwadnia, Fatima Allouch, Nadine Pirio, Julien Roger, Hélène Cattey, Sophie Fournier, Marie-Josée Penouilh, Charles H. Devillers, Dominique Lucas, Daoud Naoufal, Ridha Ben Salem, and Jean-Cyrille Hierso|2013|Organometallics|32|5784|doi:10.1021/om400317s
CCDC 1433508: Experimental Crystal Structure Determination
Related Article: Fatima Allouch, Nejib Dwadnia, Nikolay V. Vologdin, Yurii V. Svyaschenko, Hélène Cattey, Marie-José Penouilh, Julien Roger, Daoud Naoufal, Ridha Ben Salem, Nadine Pirio, Jean-Cyrille Hierso|2015|Organometallics|34|5015|doi:10.1021/acs.organomet.5b00601
CCDC 1485962: Experimental Crystal Structure Determination
Related Article: Nejib Dwadnia, Julien Roger, Nadine Pirio, Hélène Cattey, Ridha Ben Salem, Jean-Cyrille Hierso|2017|Chem.Asian J.|12|459|doi:10.1002/asia.201601583