A General Procedure for the Synthesis of Enones via Gold-Catalyzed Meyer-Schuster Rearrangement of Propargylic Alcohols at Room Temperature

Meyer Schuster rearrangements of propargylic alcohols take place readily at room temperature in toluene with 1-2 mol PPh3AuNTf2, in the presence of 0.2 equiv of 4-methoxyphenylboronic acid or 1 equiv of methanol. Good to excellent yields of enones can be obtained from secondary and tertiary alcohols, with high selectivity for the E-alkene in most cases. A one-pot procedure for the conversion of primary propargylic alcohols into beta-arylketones was also developed, via Meyer-Schuster rearrangement followed by Pd-catalayzed addition of a boronic acid.