A Simple, Mild and General Oxidation of Alcohols to Aldehydes or Ketones by SO2F2/K2CO3 Using DMSO as Solvent and Oxidant

Abstract A practical, general and mild oxidation of primary and secondary alcohols to carbonyl compounds proceeds in yields of up to 99% using SO 2 F 2 as electrophile in DMSO as both the oxidant and the solvent at ambient temperature. No moisture‐ and oxygen‐free conditions are required. Stoichiometric amount of inexpensive K 2 CO 3 , which generates easy to separate by‐products, is used as the base. Thus, 5‐gram scale runs proceeded in nearly quantitative yields by a simple filtration as the work‐up. The use of a polar solvent such as DMSO, which usually promotes competing Pummerer rearrangement, is also noteworthy. This protocol is compatible with a variety of common N‐, O‐, and S‐functional groups on (hetero)arene, alkene and alkyne substrates (68 examples). The protocol was applied (99% yield) to a formal synthesis of the important cholesterol‐lowering drug Rosuvastatin. magnified image