2013 Fiscal Year Final Research Report

Oxidative Carbon-Carbon Coupling Reactions Using Organocatalysis

Research Project

Project/Area Number	25620078
Research Category	Grant-in-Aid for Challenging Exploratory Research
Allocation Type	Single-year Grants
Research Field	Synthetic chemistry
Research Institution	Nagoya University
Principal Investigator	UYANIK Muhammet 名古屋大学, 工学(系)研究科(研究院), 助教 (20452188)
Project Period (FY)	2013-04-01 – 2014-03-31
Keywords	合成化学 / 有機化学 / 酸化的カップリング / ビアリール / アリールキノン
Research Abstract	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.