Département de chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7.
J Org Chem. 2009 Nov 20;74(22):8510-5. doi: 10.1021/jo901509z.
Tetraarylphosphonium (TAP)-supported DMSO, TEMPO, and DIB reagents were synthesized and used for the oxidation of alcohols, including Swern oxidation and for the alpha-acetoxylation of ketones. By taking advantage of the predictable solubility properties of the TAP unit, simple precipitation and filtration of the phosphonium moiety permit complete separation of the desired oxidation products. This paper describes the preparation of these three TAP-supported oxidative reagents and their activity in the aforementioned oxidative transformations. Furthermore, we have demonstrated that these reagents can be recycled directly when used in catalytic processes and following regeneration when used in stoichiometric processes.
四芳基膦（TAP）支持的 DMSO、TEMPO 和 DIB 试剂已被合成，并用于醇的氧化，包括 Swern 氧化和酮的α-乙酰氧基化。通过利用 TAP 单元可预测的溶解性，膦部分的简单沉淀和过滤可完全分离所需的氧化产物。本文介绍了这三种 TAP 支持的氧化试剂的制备及其在上述氧化转化中的活性。此外，我们已经证明，当这些试剂在催化过程中使用时可以直接回收，并且在使用化学计量过程时可以再生。
