Oxidative Carbon-Carbon Coupling Reactions Using Organocatalysis

联芳基化合物和芳基对苯二酚是许多生物活性化合物和功能有机材料的关键骨架。这些化合物需要高效、环保的合成方法。我们成功地实现了取代苯酚或萘酚在次碘酸盐催化下的氧化联芳基偶联反应，这些次碘酸盐以相应的碘化物和过氧化氢为共氧化剂原位生成。以中等至高产率获得了相应的联苯酚或联苯二酚。此外，根据底物的不同，还可以通过进一步的氧化得到二苯二酚或二氮杂多酚。此外，我们还成功地实现了亚碘酸盐催化过氧化氢氧化对苯二酚为对苯二酚。这些对苯二酚与芳基化合物的一锅交叉偶联反应可以在碱金属或碱土金属块状硼酸盐的催化下进行，从而以较高的产率得到相应的芳基对苯二酚。

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.