Oxidative Carbon-Carbon Coupling Reactions Using Organocatalysis

联芳基化合物和芳醌是许多生物活性化合物和功能性有机材料的关键骨架。需要高效、环保的合成方法来制备这些化合物。以碘化物和过氧化氢作为共氧化剂原位生成取代酚或萘酚，在次碘盐的催化下成功地进行了氧化联芳基偶联反应。相应的双酚类化合物或双酚类化合物中高产得。此外，根据底物的不同，还可以通过进一步氧化得到二酚醌或二萘醌。此外，我们成功地用过氧化氢在次碘酸催化下将对苯二酚氧化成醌。在碱或碱土金属块状硼酸盐的催化下，这些醌类化合物与芳基化合物进行一锅交联反应，得到相应的芳基醌类化合物，收率较高。

Biaryl compounds and arylquinones are key skeletons of many biologically active compounds and functional organic materials. The efficient and environmentally benign synthetic method for those compounds is required. We succeeded in oxidative biaryl coupling reaction of substituted phenols or naphthols catalyzed by hypoiodite salts, which were generated in situ from the corresponding iodide and aqueous hydrogen peroxide as a co-oxidant. The corresponding biphenols or binaphthols were obtained in moderate to high yields. Additionally, depending on the substrates, diphenoquinones or dinaphthoquinones were also obtained by further oxidations. Moreover, we succeeded in hypoiodite-catalyzed oxidation of hydroquinones to quinones with aqueous hydrogen peroxide. The subsequent one-pot cross coupling of these quinones with aryl compounds could be achieved catalyzed by alkali or alkaline earth metal bulky borate salts to give the corresponding arylquinones in good yields.