Abstract
AbstractA practical, general and mild oxidation of primary and secondary alcohols to carbonyl compounds proceeds in yields of up to 99% using SO2F2 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 K2CO3, 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
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