Abstract
AbstractThe hitherto unreported ability of the methylsulfinyl carbanion (dimsyl anion) to generate acyl anion equivalents is described. The dimsyl anion, in fact, efficiently catalyzes chemoselective intermolecular cross‐benzoin condensations of diaryl α‐diketones (benzils) with various aromatic and aliphatic aldehydes to give the corresponding aryl‐aryl and aryl‐alkyl benzoin benzoates in an atom‐economic fashion. The dimsyl anion acts as an environmentally friendly alternative to the toxic cyanide anion and it is obtained by in situ deprotonation of dimethyl sulfoxide (DMSO) solvent with a catalytic amount of a strong base, potassium tert‐butoxide (t‐BuOK) the optimal promoter. The assumption that the methylsulfinyl carbanion is the active catalyst in the title transformation is supported by electrospray ionization mass spectrometry (ESI‐MS) experiments.magnified image
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