Abstract
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 β-arylketones was also developed, via Meyer-Schuster rearrangement followed by Pd-catalayzed addition of a boronic acid.(Figure Presented)
Original language | English |
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Pages (from-to) | 1479-1482 |
Number of pages | 4 |
Journal | Journal of Organic Chemistry |
Volume | 76 |
Issue number | 5 |
Early online date | 25 Jan 2011 |
DOIs | |
Publication status | Published - 4 Mar 2011 |
Externally published | Yes |