Oxidative esterification of aldehydes using mesoionic 1,2,3-triazolyl carbene organocatalysts.

The synthesis and catalytic activity of a new class of 1,2,3-triazolyl N-heterocyclic carbene organocatalysts is described. These new catalysts chemoselectively facilitate the oxidative esterification of aldehydes. NMR acidity studies show an inverse correlation between triazolium acidity and reactivity. Kinetic studies show that the resting state of the catalyst involves a NHC-aldehyde adduct. A catalytically active intermediate was synthesized and characterized by X-ray diffraction as the initial carbene-aldehyde adduct.