Highly selective alcohol oxidation by polyvinyl cyanuric chloride in DMSO: a metal- and catalyst-free approach

The present study introduces polyvinyl cyanuric chloride (PVCC) as an efficient reagent for the selective catalyst/metal-free oxidation of primary and secondary alcohols to the corresponding aldehyde and ketones in the presence of dimethyl sulfoxide (DMSO) as a solvent and oxidant. PVCC was derived from polyvinyl alcohol (PVA) and synthesized simply in the presence of cyanuric chloride (2,4,6-Trichloro-1,3,5-triazine or TCT) in one step. The oxidation was conducted at 50 °C in the absence of any other external oxidant. All 25 entries under study achieved high selectivity, up to 98%, within 30 to 120 min. PVCC could be recovered, re-activated by POCl₃/PCl₅ and re-used for at least five consecutive runs without any considerable reactivity loss. The oxidation system was inert toward oxidation of aldehydes.

A highly selective protocol has been developed for alcohol oxidation to aldehyde using polyvinyl cyanuric chloride and DMSO as a solid reagent and oxidant/solvent respectively.