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Carbon–Phosphorus Coupling from C^N Cyclometalated Au III Complexes
Author(s) -
Bonsignore Riccardo,
Thomas Sophie R.,
Klooster Wim T.,
Coles Simon J.,
Jenkins Robert L.,
Bourissou Didier,
Barone Giampaolo,
Casini Angela
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201905392
Subject(s) - phosphonium , chemistry , denticity , reactivity (psychology) , medicinal chemistry , coupling reaction , coupling (piping) , phosphorus , stereochemistry , combinatorial chemistry , metal , organic chemistry , catalysis , medicine , mechanical engineering , alternative medicine , pathology , engineering
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.