0000000001302784
AUTHOR
Didier Bourissou
Cyclometalated Au(III) Complexes for Cysteine Arylation in Zinc Finger Protein Domains: Towards Controlled Reductive Elimination
With the aim of exploiting the use of organometallic species for the efficient modification of proteins through C-atom transfer, the gold-mediated cysteine arylation through a reductive elimination process occurring from the reaction of cyclometalated AuIII C^N complexes with a zinc finger peptide (Cys2His2 type) is here reported. Among the four selected AuIII cyclometalated compounds, the [Au(CCON)Cl2] complex featuring the 2-benzoylpyridine (CCON) scaffold was identified as the most prone to reductive elimination and Cys arylation in buffered aqueous solution (pH 7.4) at 37 °C by high-resolution LC electrospray ionization mass spectrometry. DFT and quantum mechanics/molecular mechanics (Q…
Carbon–Phosphorus Coupling from C^N Cyclometalated Au III Complexes
Abstract With the aim of exploiting new organometallic species for cross‐coupling reactions, we report here on the AuIII‐mediated Caryl−P bond formation occurring upon reaction of C^N cyclometalated AuIII complexes with phosphines. The [Au(C^N)Cl2] complex 1 featuring the bidentate 2‐benzoylpyridine (CCON) scaffold was found to react with PTA (1,3,5‐triaza‐7‐phosphaadamantane) under mild conditions, including in water, to afford the corresponding phosphonium 5 through C−P reductive elimination. A mechanism is proposed for the title reaction based on in situ 31P{1H} NMR and HR‐ESI‐MS analyses combined with DFT calculations. The C−P coupling has been generalized to other C^N cyclometalated Au…
ortho-(Dimesitylboryl)phenylphosphines: Positive Boryl Effect in the Palladium-Catalyzed Suzuki-Miyaura Coupling of 2-Chloropyridines
The presence of ortho-dimesitylboryl moiety in the catalyst is crucial to enhance the catalytic performance.
Planar-Chiral 1,1 '-Diboryl Metallocenes: Diastereoselective Synthesis from Boryl Cyclopentadienides and Spin Density Analysis of a Diborylcobaltocene
International audience; The reaction of nonsubstituted alkali metal cyclopentadienides with haloboranes leads to similar to 90:10 mixtures of isomeric diene products that can be deprotonated to give simple boryl cyclopentadienides. We extended this transformation to the sterically hindered lithium tert-butylcyclopentadienide 1 using FBMe(s)2 (Mes = 2,4,6-trimethylphenyl) and ClBCy2 as electrophiles. The boryl group is selectively introduced in the remote position to minimize steric congestion. The new boryl dienes are obtained as mixtures of isomers, and subsequent deprotonation with MeLi or LiHMDS affords the lithium 1,3-disubstituted cyclopentadienides Sa,b in yields over 95%. Direct asse…
C−C Cross-Couplings from a Cyclometalated Au(III) C∧ N Complex: Mechanistic Insights and Synthetic Developments
Abstract In recent years, the reactivity of gold complexes was shown to extend well beyond π‐activation and to hold promises to achieve selective cross‐couplings in several C−C and C−E (E=heteroatom) bond forming reactions. Here, with the aim of exploiting new organometallic species for cross‐coupling reactions, we report on the Au(III)‐mediated C(sp2)−C(sp) occurring upon reaction of the cyclometalated complex [Au(CCH2N)Cl2] (1, CCH2N=2‐benzylpyridine) with AgPhCC. The reaction progress has been monitored by NMR spectroscopy, demonstrating the involvement of a number of key intermediates, whose structures have been unambiguously ascertained through 1D and 2D NMR analyses (1H, 13C, 1H‐1H CO…
A sterically congested 1,2-diphosphino-1'-boryl-ferrocene: synthesis, characterization and coordination to platinum.
International audience; A new class of tritopic ferrocene-based ambiphilic compound has been prepared by assembling diphosphino- and boryl-substituted cyclopentadienides at iron. The presence of five sterically demanding substituents on the ferrocene platform induces conformation constraints, as apparent from XRD and NMR data, but does not prevent chelating coordination to platinum. The Lewis acid moiety is pendant in both the free ligand and the platinum complex.
CCDC 1941496: Experimental Crystal Structure Determination
Related Article: Riccardo Bonsignore, Sophie R. Thomas, Wim T. Klooster, Simon J. Coles, Robert L. Jenkins, Didier Bourissou, Giampaolo Barone, Angela Casini|2020|Chem.-Eur.J.|26|4226|doi:10.1002/chem.201905392
CCDC 1941494: Experimental Crystal Structure Determination
Related Article: Riccardo Bonsignore, Sophie R. Thomas, Wim T. Klooster, Simon J. Coles, Robert L. Jenkins, Didier Bourissou, Giampaolo Barone, Angela Casini|2020|Chem.-Eur.J.|26|4226|doi:10.1002/chem.201905392
CCDC 2082255: Experimental Crystal Structure Determination
Related Article: Riccardo Bonsignore, Sophie R. Thomas, Mathilde Rigoulet, Christian Jandl, Alexander P��thig, Didier Bourissou, Giampaolo Barone, Angela Casini|2021|Chem.-Eur.J.|27|14322|doi:10.1002/chem.202102668
CCDC 1947336: Experimental Crystal Structure Determination
Related Article: Riccardo Bonsignore, Sophie R. Thomas, Wim T. Klooster, Simon J. Coles, Robert L. Jenkins, Didier Bourissou, Giampaolo Barone, Angela Casini|2020|Chem.-Eur.J.|26|4226|doi:10.1002/chem.201905392
CCDC 1474154: Experimental Crystal Structure Determination
Related Article: Emmanuel Lerayer, Patrice Renaut, Stéphane Brandès, Hélène Cattey, Paul Fleurat-Lessard, Ghenwa Bouhadir, Didier Bourissou, and Jean-Cyrille Hierso|2017|Inorg.Chem.|56|1966|doi:10.1021/acs.inorgchem.6b02510
CCDC 2082254: Experimental Crystal Structure Determination
Related Article: Riccardo Bonsignore, Sophie R. Thomas, Mathilde Rigoulet, Christian Jandl, Alexander Pöthig, Didier Bourissou, Giampaolo Barone, Angela Casini|2021|Chem.-Eur.J.|27|14322|doi:10.1002/chem.202102668
CCDC 1902394: Experimental Crystal Structure Determination
Related Article: Emmanuel Lerayer, Patrice Renaut, Julien Roger, Nadine Pirio, Hélène Cattey, Paul Fleurat-Lessard, Maxime Boudjelel, Stéphane Massou, Ghenwa Bouhadir, Didier Bourissou, Jean-Cyrille Hierso|2019|Dalton Trans.|48|11191|doi:10.1039/C9DT01921A
CCDC 2082253: Experimental Crystal Structure Determination
Related Article: Riccardo Bonsignore, Sophie R. Thomas, Mathilde Rigoulet, Christian Jandl, Alexander Pöthig, Didier Bourissou, Giampaolo Barone, Angela Casini|2021|Chem.-Eur.J.|27|14322|doi:10.1002/chem.202102668
CCDC 1902395: Experimental Crystal Structure Determination
Related Article: Emmanuel Lerayer, Patrice Renaut, Julien Roger, Nadine Pirio, Hélène Cattey, Paul Fleurat-Lessard, Maxime Boudjelel, Stéphane Massou, Ghenwa Bouhadir, Didier Bourissou, Jean-Cyrille Hierso|2019|Dalton Trans.|48|11191|doi:10.1039/C9DT01921A
CCDC 1968702: Experimental Crystal Structure Determination
Related Article: Riccardo Bonsignore, Sophie R. Thomas, Wim T. Klooster, Simon J. Coles, Robert L. Jenkins, Didier Bourissou, Giampaolo Barone, Angela Casini|2020|Chem.-Eur.J.|26|4226|doi:10.1002/chem.201905392
CCDC 2096758: Experimental Crystal Structure Determination
Related Article: Riccardo Bonsignore, Sophie R. Thomas, Mathilde Rigoulet, Christian Jandl, Alexander Pöthig, Didier Bourissou, Giampaolo Barone, Angela Casini|2021|Chem.-Eur.J.|27|14322|doi:10.1002/chem.202102668
CCDC 1474155: Experimental Crystal Structure Determination
Related Article: Emmanuel Lerayer, Patrice Renaut, Stéphane Brandès, Hélène Cattey, Paul Fleurat-Lessard, Ghenwa Bouhadir, Didier Bourissou, and Jean-Cyrille Hierso|2017|Inorg.Chem.|56|1966|doi:10.1021/acs.inorgchem.6b02510