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946 results on '"Bourissou, Didier"'

5. Diazo Decomposition and Carbene Transfer Mediated by a Pincer Gold(III) Complex

Author

Wei, Rui, Ma, Liyao, Mallet-Ladeira, Sonia, and Bourissou, Didier

Abstract

The pincer triflimide Au(III) complex (N∧C∧C)AuNTf22is shown to decompose aryl diazo compounds Ph2CN2, (Dmp)CN2H (Dmp = 2,6-dimesitylphenyl), and (p-F3CPh)CN2H and generate the corresponding Au(III) carbene complexes. Azine compounds resulting from carbene/diazo coupling have been isolated and structurally characterized. Carbene transfer to external reagents such as trimethylsilyl azide, methanol, and styrene affords the corresponding imine, ether, and cyclopropane under both stoichiometric and catalytic conditions.

Published
2024
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10. Synthesis and Organo‐Catalyzed Ring‐Opening of a Six‐Membered Heterocycle Combining Phosphonate and Ester Functions.

Author

Ungpittagul, Thasanaporn, Virachotikul, Arnut, Monot, Julien, Martín‐Vaca, Blanca, and Bourissou, Didier

Subjects
RING-opening polymerization, SCISSION (Chemistry), LIVING polymerization, ESTERS, SULFONIC acids, FLUOROFORM
Abstract

The synthesis of a difunctional P‐heterocycle combining phosphonate and ester moieties in a six‐membered ring is described. Using trifluoromethane sulfonic acid HOTf as organocatalyst, ring‐opening with neopentyl alcohol readily occurs with complete selectivity for O‐acyl bond cleavage. In turn, ring‐opening polymerization proceeds in a controlled manner when an excess of P‐heterocycle is used. Copolymerization with ϵ‐caprolactone is also reported and semi‐batch conditions are shown to enable regular incorporation of the phosphonate moieties along the polymer chains. [ABSTRACT FROM AUTHOR]

Published
2024
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17. Base‐Triggered Oxidative Addition to Gold

Author

Marelli, Enrico, primary, Monot, Julien, additional, Martin‐Vaca, Blanca, additional, Mallet‐Ladeira, Sonia, additional, García‐Rodeja, Yago, additional, Miqueu, Karinne, additional, and Bourissou, Didier, additional

Published
2023
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19. Frontispiz: Square‐Planar Anionic Pt 0 Complexes

Author

Kameo, Hajime, primary, Tanaka, Yudai, additional, Shimoyama, Yoshihiro, additional, Izumi, Daisuke, additional, Matsuzaka, Hiroyuki, additional, Nakajima, Yumiko, additional, Lavedan, Pierre, additional, Le Gac, Arnaud, additional, and Bourissou, Didier, additional

Published
2023
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22. Energetics of key Au(III)-substrate adducts relevant to catalytic hydroarylation of alkynes.

Author

Regnacq, Matthieu, Lesage, Denis, Holmsen, Marte S. M., Miqueu, Karinne, Bourissou, Didier, and Gimbert, Yves

Subjects
ALKYNES, THRESHOLD energy, MASS spectrometry
Abstract

(P,C)-cyclometalated Au(III) complexes have shown remarkable ability to catalyze the intermolecular hydroarylation of alkynes. Evidence of an outer-sphere mechanism has been provided in a previous study and is confirmed here by analysing the experimental data and DFT calculations. In this work, we propose evaluation of critical energies of dissociation of Au(III) complexes with different substrates via energyresolved mass spectrometry (ERMS) experiments and kinetic modelling. The kinetic model is based on a multi-collisional approach. On the one hand, the classification confirms the mechanism previously proposed; on the other hand, it supports the collisional model and its application to particularly fragile adducts. [ABSTRACT FROM AUTHOR]

Published
2023
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24. Square‐Planar Anionic Pt0 Complexes

Author

Kameo, Hajime, primary, Tanaka, Yudai, additional, Shimoyama, Yoshihiro, additional, Izumi, Daisuke, additional, Matsuzaka, Hiroyuki, additional, Nakajima, Yumiko, additional, Lavedan, Pierre, additional, Le Gac, Arnaud, additional, and Bourissou, Didier, additional

Published
2023
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25. Square‐Planar Anionic Pt 0 Complexes

Author

Kameo, Hajime, primary, Tanaka, Yudai, additional, Shimoyama, Yoshihiro, additional, Izumi, Daisuke, additional, Matsuzaka, Hiroyuki, additional, Nakajima, Yumiko, additional, Lavedan, Pierre, additional, Le Gac, Arnaud, additional, and Bourissou, Didier, additional

Published
2023
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29. σ‐Cyclopropyl to π‐Allyl Rearrangement at AuIII.

Author

Holmsen, Marte S. M., Vesseur, David, García‐Rodeja, Yago, Miqueu, Karinne, and Bourissou, Didier

Subjects
DENSITY functional theory, CLAISEN rearrangement
Abstract

The possibility for AuIII σ‐cyclopropyl complexes to undergo ring‐opening and give π‐allyl complexes was interrogated. The transformation was first evidenced within (P,C)‐cyclometalated complexes, it occurs within hours at −50 °C. It was then generalized to other ancillary ligands. With (N,C)‐cyclometalated complexes, the rearrangement occurs at room temperature while it proceeds already at −80 °C with a dicationic (P,N)‐chelated complex. Density Functional Theory (DFT) calculations shed light on the mechanism of the transformation, a disrotatory electrocyclic ring‐opening. Intrinsic Bond Orbital (IBO) analysis along the reaction profile shows the cleavage of the distal σ(CC) bond to give a π‐bonded allyl moiety. Careful inspection of the structure and bonding of cationic σ‐cyclopropyl complexes support the possible existence of C−C agostic interactions at AuIII. [ABSTRACT FROM AUTHOR]

Published
2023
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30. σ‐Cyclopropyl to π‐Allyl Rearrangement at AuIII.

Author

Holmsen, Marte S. M., Vesseur, David, García‐Rodeja, Yago, Miqueu, Karinne, and Bourissou, Didier

Subjects
DENSITY functional theory, CLAISEN rearrangement
Abstract

The possibility for AuIII σ‐cyclopropyl complexes to undergo ring‐opening and give π‐allyl complexes was interrogated. The transformation was first evidenced within (P,C)‐cyclometalated complexes, it occurs within hours at −50 °C. It was then generalized to other ancillary ligands. With (N,C)‐cyclometalated complexes, the rearrangement occurs at room temperature while it proceeds already at −80 °C with a dicationic (P,N)‐chelated complex. Density Functional Theory (DFT) calculations shed light on the mechanism of the transformation, a disrotatory electrocyclic ring‐opening. Intrinsic Bond Orbital (IBO) analysis along the reaction profile shows the cleavage of the distal σ(CC) bond to give a π‐bonded allyl moiety. Careful inspection of the structure and bonding of cationic σ‐cyclopropyl complexes support the possible existence of C−C agostic interactions at AuIII. [ABSTRACT FROM AUTHOR]

Published
2023
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37. Square‐Planar Anionic Pt0 Complexes.

Author

Kameo, Hajime, Tanaka, Yudai, Shimoyama, Yoshihiro, Izumi, Daisuke, Matsuzaka, Hiroyuki, Nakajima, Yumiko, Lavedan, Pierre, Le Gac, Arnaud, and Bourissou, Didier

Subjects
X-ray photoelectron spectroscopy, LEWIS bases, LEWIS acids, X-ray diffraction, OXIDATION states, LIGANDS (Chemistry), SCHIFF bases
Abstract

A T‐shaped Pt0 complex with a diphosphine‐borane (DPB) ligand was prepared. The Pt→B interaction enhances the electrophilicity of the metal and triggers the addition of Lewis bases to give the corresponding tetracoordinate complexes. For the first time, anionic Pt0 complexes are isolated and structurally authenticated. X‐ray diffraction analyses show the anionic complexes [(DPB)PtX]− (X=CN, Cl, Br, I) to be square‐planar. The d10 configuration and Pt0 oxidation state of the metal were unambiguously established by X‐ray photoelectron spectroscopy and DFT calculations. The coordination of Lewis acids as Z‐type ligands is a powerful mean to stabilize elusive electron‐rich metal complexes and achieve uncommon geometry. [ABSTRACT FROM AUTHOR]

Published
2023
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49. Nucleophilic Addition to pi-Allyl Gold(III) Complexes: Evidence for Direct and Undirect Paths

Author

Miqueu, Karinne, Rodriguez, Jessica, Martinsen Holmsen, Marte Sofie, García-Rodeja, Yago, Daiann Sosa Carrizo, Eric, Lavedan, Pierre, Mallet-Ladeira, Sonia, Bourissou, Didier, Institut des sciences analytiques et de physico-chimie pour l'environnement et les materiaux (IPREM), Université de Pau et des Pays de l'Adour (UPPA)-Centre National de la Recherche Scientifique (CNRS), Department of Chemistry [Oslo], Faculty of Mathematics and Natural Sciences [Oslo], University of Oslo (UiO)-University of Oslo (UiO), Laboratoire Hétérochimie Fondamentale et Appliquée (LHFA), Institut de Chimie de Toulouse (ICT-FR 2599), Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS), Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut National Polytechnique (Toulouse) (Toulouse INP), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3)

Subjects
[CHIM]Chemical Sciences
Abstract

International audience; pi-Allyl complexes play a prominent role in organometallic chemistry and have attracted considerable attention, in particular the pi-allyl Pd(II) complexes which are key intermediates in the Tsuji-Trost allylic substitution reaction. Despite the huge interest for pi-complexes of gold, pi-allyl Au(III) complexes were only authenticated very recently. Herein, we report the reactivity of (P,C)-cyclometallated Au(III) pi-allyl complexes towards -diketo enolates. Behind an apparently trivial outcome, ie the formation of the corresponding allylation products, meticulous NMR studies combined with DFT calculations revealed a complex and rich mechanistic picture. Nucleophilic attack can occur at the central and terminal positions of the pi-allyl as well as the metal itself. All paths are observed and are actually competitive, whereas addition to the terminal positions largely prevails for Pd(II). Auracyclobutanes and pi-alkene Au(I) complexes were authenticated spectroscopically and crystallographically, Au(III) pi-allyl complexes were unambiguously characterized by multi-nuclear NMR spectroscopy. Nucleophilic additions to the central position of the pi-allyl and to gold are reversible. Over time, the auracyclobutanes and the Au(III) pi-allyl complexes evolve into the pi-alkene Au(I) complexes and release the C-allylation products. The relevance of auracyclobutanes in gold-mediated cyclopropanation was demonstrated by inducing CC coupling with iodine. The molecular orbitals of the pi-allyl Au(III) complexes were analyzed in-depth and the reaction profiles for the addition of pi-diketo enolates were thoroughly studied by DFT. Special attention was devoted to the regioselectivity of the nucleophilic attack, but CC coupling to give the allylation products was also considered to give a complete picture of the reaction progress.

Published
2021

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