Preparation of 2-arylpropanoic acids by oxidative aryl migration in (β-aryl-β-hydroxy)alkyl phenyl selenides

Abstract

Oxidation of diastereoisomeric mixtures of 1-aryl-1-hydroxyprop-2-yl phenyl selenides, prepared either by phenylselenenylation of propiophenones followed by reduction or by treatment of benzaldehyde with α-(phenylseleno)ethyl anion, with an excess of meta-chloroperbenzoic acid in methanol at 25 °C for 24 h or at reflux for 2 h affords methyl 2-arylpropanoates almost quantitatively. Similar treatment in tetrahydrofuran at 25 °C for 24 h results in a direct formation of 2-arylpropanoic acids in high yields.