Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 5, Pages 1479-1482Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo102263t
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Funding
- EPSRC [EP/E052789/1, EP/G040680/1]
- GlaxoSmithKline
- Engineering and Physical Sciences Research Council [EP/E052789/1] Funding Source: researchfish
- EPSRC [EP/E052789/1] Funding Source: UKRI
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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.
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