Reductive esterification of aromatic aldehydes using Zn/Ac2O/imidazole or Zn/Yb(OTf)3/(RCO)2O system

Benzaldehydes are reduced by metallic zinc in the presence of Ac2O and imidazole, giving the corresponding benzyl acetates in good yields. Reductive esterification of aromatic aldehydes is also carried out via gem-diacetoxy compounds. Carbonyl compounds are readily converted to the gem-diacyloxy compounds in excellent yields on treatment with 2 molar amounts of acid anhydride and 10 mol% of Yb(OTf)(3) in MeCN at room temperature. Thus-formed diacyloxy compounds derived from aromatic aldehydes are reduced in situ by metallic zinc to afford the corresponding esters. (C) 2003 Elsevier Ltd. All rights reserved.