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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 AuIII complexes and other tertiary phosphines. Overall, this work provides new insights into the reactivity of cyclometalated AuIII compounds and establishes initial structure–activity relationships to develop AuIII‐mediated C−P cross‐coupling reactions.
Highlights
With the aim of exploiting new organometallic species for cross-coupling reactions, we report here on the AuIII-mediated CarylÀP bond formation occurring upon reaction of C^N cyclometalated AuIII complexes with phosphines
The use of the redox pair AuI/AuIII has gained interest to trigger new carbon–carbon and carbon–heteroatom bond-forming reactions.[2a,3] Over the last few years, examples of fast CÀC cross-coupling reactions under mild conditions have been reported through AuI/AuIII cycles.[4]
We have discovered that AuIII C^N complexes achieve CÀ P cross-coupling reactions under mild conditions
Summary
With the aim of exploiting new organometallic species for cross-coupling reactions, we report here on the AuIII-mediated CarylÀP bond formation occurring upon reaction of C^N cyclometalated AuIII complexes with phosphines. CÀP coupling upon reaction of the C^N cyclometalated complex 1 with PTA (1,3,5-triaza-7-phosphaadamantane).
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