Abstract

A mild and highly chemoselective approach to oxidation of allylic, electron rich/deficient benzylic, and heterocyclic alcohols employing catalytic quantities of K2[OsO2(OH)4] (3mol%) and chloramine-T (50mol%) is described. The protocol offers short reaction times (25min–2h), controlled oxidation, and tolerance to a variety of substrates. A systematic mechanistic study based on the LC-ESI-MS/MS reveals the presence of imidotriooxoosmium species which further reacts with alcohol to give the oxidized product.

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