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 % PPh(3)AuNTf(2), 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 β-arylketones was also developed, via Meyer-Schuster rearrangement followed by Pd-catalayzed addition of a boronic acid.
Department of Chemistry, University College London, Christopher Ingold Laboratories, 20, Gordon Street, London WC1H 0AJ, UK.
Matthew N
MN
Pennell
Matthew G
MG
Unthank
Peter
P
Turner
Tom D
TD
Sheppard
D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature
D000480:Alkynes; D007659:Ketones; D020005:Propanols; D006046:Gold; C028255:propargyl alcohol