A Simple, Mild and General Oxidation of Alcohols to Aldehydes or Ketones by SO 2 F 2 /K 2 CO 3 Using DMSO as Solvent and Oxidant

作者：Gao‐Feng Zha, Wan‐Yin Fang, Jing Leng, Hua‐Li Qin · 发表于：Advanced Synthesis & Catalysis · 年份：2019 · DOI：10.1002/adsc.201900104 · 被引用次数：56 · 研究领域：Chemical Synthesis and Reactions、Oxidative Organic Chemistry Reactions、Synthesis and Catalytic Reactions

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