Mercury in Organic Chemistry. 18. Synthesis of Symmetrical Divinyl and Diaryl Ketones via Rhodium-Catalyzed Carbonylation of Vinyl- and Arylmercurials

Article abstract of DOI:10.1021/jo01307a022

Vinylmercuric chlorides readily react with rhodium(I) and rhodium(III) catalysts and carbon monoxide to give excellent yields of divinyl ketones.The best reaction conditions are 0.5 mol percent 2 and 2 equiv of lithium chloride under 1 atm of carbon monoxide at room temperature.This rhodium catalyst also provides improved yields of diaryl ketones from arylmercurials at 70 deg C under 1000-1500 psi of carbon monoxide pressure.Organorhodium compounds are presumed to be intermediates in these reactions.