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Carbon–Phosphorus Coupling from C^N Cyclometalated Au<sup>III</sup> Complexes

Riccardo Bonsignore, Sophie R. Thomas, Wim T. Klooster, Simon J. Coles, Robert L. Jenkins, Didier Bourissou, Giampaolo Barone, Angela Casini

2020Chemistry - A European Journal25 citationsDOIOpen Access PDF

Abstract

Abstract With the aim of exploiting new organometallic species for cross‐coupling reactions, we report here on the Au III ‐mediated C aryl −P bond formation occurring upon reaction of C^N cyclometalated Au III complexes with phosphines. The [Au(C^N)Cl 2 ] complex 1 featuring the bidentate 2‐benzoylpyridine (C CO N) 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 31 P{ 1 H} NMR and HR‐ESI‐MS analyses combined with DFT calculations. The C−P coupling has been generalized to other C^N cyclometalated Au III complexes and other tertiary phosphines. Overall, this work provides new insights into the reactivity of cyclometalated Au III compounds and establishes initial structure–activity relationships to develop Au III ‐mediated C−P cross‐coupling reactions.

Topics & Concepts

PhosphoniumChemistryReactivity (psychology)DenticityArylCoupling reactionMedicinal chemistryStereochemistryCoupling (piping)Organometallic chemistryPhosphorusCatalysisAlkylPolymer chemistryOrganic chemistryMetalMaterials scienceMetallurgyAlternative medicinePathologyMedicineCatalytic Cross-Coupling ReactionsCatalytic Alkyne ReactionsCatalytic C–H Functionalization Methods
Carbon–Phosphorus Coupling from C^N Cyclometalated Au<sup>III</sup> Complexes | Litcius