Abstract

which are Lewis base catalysts, represent aversatile class of organocatalysts that allow the addition of avariety of different electrophiles to carbonyl or Michaelacceptors via Umpolung or Breslow intermediates. Thebenzoin condensation (BC) reaction is a representativeexample of the Umpolung process in which a NHC is usedto generate an acyl anion via polarity reversal of aldehydesthat can react with other aldehydes. Ugai and co-workersreported in 1943 that thiazolium salts, NHC precatalysts, cancatalyze the self-condensation of benzaldehyde to givebenzoin.

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