Organic synthesis
Gold C–N/C–O coupling without extra oxidants
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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.
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Gold C–N/C–O coupling without extra oxidants
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t-Butoxide coupling gave 4% yield (2-propoxide 21%).
This trend could be further extrapolated to more sterically demanding alkoxides such as 2-propoxide ( 1ad ) and tert -butoxide ( 1ae ) giving yields of 21% and 4%, respectively (, entries 7 and 8).
Desired C–N product 1ac increased up to 78% after 48 h.
moderate 56% yield of the desired coupling product 1ac was obtained, which could be increased up to 78% after 48 h (, entry 6).
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.
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