Matsubara Hiroshi, Maegawa Takahiko, Kita Yasuaki, Yokoji Takato, Nomoto Akihiro
Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan.
Org Biomol Chem. 2014 Aug 7;12(29):5442-7. doi: 10.1039/c4ob00783b.
1,4-Benzoquinone derivatives bearing trifluoromethyl, perfluorobutyl and perfluorohexyl groups were prepared and employed in the deprotection of silyl ethers. The fluorous character of these compounds was examined by measuring the partition coefficient between the fluorous and organic solvents. The benzoquinone derivatives showed significant fluorous character, indicating that they can be recovered from the reaction mixtures using a fluorous/organic biphasic system. The oxidising ability of the fluorous benzoquinones was estimated by cyclic voltammetry, and these compounds were found to be strong oxidisers. The fluorous benzoquinones were utilised in the oxidative desilylation of silyl ethers to afford the deprotected alcohols in high yield. In addition, the reduced fluorous benzoquinones were recovered from the reaction mixtures in good yields using a fluorous/organic biphasic system.
制备了带有三氟甲基、全氟丁基和全氟己基的1,4-苯醌衍生物，并将其用于硅醚的脱保护反应。通过测量这些化合物在氟代溶剂和有机溶剂之间的分配系数来考察其氟代性质。苯醌衍生物表现出显著的氟代性质，这表明它们可以使用氟代/有机双相体系从反应混合物中回收。通过循环伏安法评估了氟代苯醌的氧化能力，发现这些化合物是强氧化剂。氟代苯醌被用于硅醚的氧化脱硅反应，以高收率得到脱保护的醇。此外，使用氟代/有机双相体系可以从反应混合物中高收率地回收还原后的氟代苯醌。
