Department of Chemistry, Innovative Drug Research Center, Shanghai University, 99 Shangda Road, 200444, Shanghai, P. R. China.
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, 200032, Shanghai, P. R. China.
Chem Asian J. 2022 Jul 15;17(14):e202200190. doi: 10.1002/asia.202200190. Epub 2022 Jun 10.
The classical Pummerer rearrangement of 2,2,2-trifluoroethylaryl sulfoxide with trifluoracetic anhydride (TFAA) affords the S,O-acetal efficiently. In the presence of trifluoracetic acid (TFA) as the co-solvent, the S,O-acetal can regenerate reactive thionium intermediate of Pummerer rearrangement. When employing arenes as nucleophiles, this strategy produces corresponding 1-thiyl-2,2,2-trifluoroethyl arenes with excellent yields under metal-free conditions.
用三氟乙酸酐（TFAA）对 2,2,2-三氟乙基芳基砜进行经典的 Pummerer 重排，可以有效地得到 S,O-缩醛。在三氟乙酸（TFA）作为共溶剂的存在下，S,O-缩醛可以再生 Pummerer 重排的反应性硫翁中间体。当使用芳基作为亲核试剂时，在无金属条件下，该策略可以以优异的收率得到相应的 1-硫基-2,2,2-三氟乙基芳基。
