DMSO/I-2 mediated C-C bond cleavage of alpha-ketoaldehydes followed by C-O bond formation: a metal-free approach for one-pot esterification

A novel and efficient I-2/DMSO mediated metal-free strategy is presented for the direct C-C bond cleavage of aryl-/heteroaryl- or aliphatic alpha-ketoaldehydes by C-2-decarbonylation and C-1-carbonyl oxidation to give the corresponding carboxylic acids followed by esterification in one pot, offering excellent yields in both the steps. Here, DMSO acts as the oxygen source/oxidant and this reaction works very well under both conventional heating and microwave irradiation. This is a very simple and convenient protocol.