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Synthesis 2004(11): 1767-1770
DOI: 10.1055/s-2004-829119
DOI: 10.1055/s-2004-829119
PAPER
© Georg Thieme Verlag Stuttgart · New York
Chemoselective RuO4 Oxidation of Phenyl or p-Methoxyphenyl Groups to Carboxylic Acid Functions in the Presence of a Tetrahydropyran Ring
Further Information
Received
8 March 2004
Publication Date:
01 July 2004 (online)
Publication History
Publication Date:
01 July 2004 (online)
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Abstract
We describe the first example of a chemoselective oxidation of phenyl and p-methoxyphenyl groups to carboxylic acid functions in the presence of a tetrahydropyran ring, using 0.02 mol% of RuCl3 and a co-oxidant. The use of NaIO4 as co-oxidant in H2O-CH3CN-CCl4 as the solvent system led to diketone 7. The change of the co-oxidant from sodium periodate to periodic acid and removal of water from the solvent system led to carboxylic acid 2 in good yield as the sole product .
Key words
oxidation - catalysis - aromatic - ruthenium tetroxide - tetrahydropyran - Prins reaction - Barbier reaction
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