Organic synthesis
Gold C–N/C–O coupling without extra oxidants
Open access · cc by · source: Europe PMC
Cyclometalated gold catalyzes aryl C–N and C–O coupling in air/water by Au(I)/Au(III) oxidative addition, without sacrificial I(III) or F+ oxidants.
Key findings
First oxidant-free gold-catalyzed C–N couplings, plus C–O with aliphatic alcohols and water. Methoxide/ethanol competition favors smaller, more acidic alkoxides; t-butoxide gives only 4%. Aniline coupling reached 78% after 48 h. Air and water are tolerated.
Methodology
Authors used [Au(NCMe)IPr]+ with 2-(2-halophenyl)pyridine substrates, coupled alkoxides, water/hydroxide, anilines and amides, isolated C–N cyclometalated Au(III) species, and showed nucleophile acidity controls product identity.
Limitations
Broad unactivated aryl chloride scope like modern Pd Buchwald–Hartwig is not claimed; many examples use directing 2-pyridyl assistance.
How this study connects
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