Evaluation of nitroxide radical catalyst activity in the C-H activation step of the oxidative coupling between acridone derivatives and nitromethane

2016 Fiscal Year Final Research Report

• Project/Area Number: 26810055
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Yokohama National University
• Principal Investigator: Gotoh Hiroaki 横浜国立大学, 大学院工学研究院, 准教授 (80635235)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Keywords: 有機分子触媒 / ラジカル / 反応機構解析 / ニトロキシドラジカル / 酸素

Outline of Final Research Achievements

Organocatalysts have been the subject of intense research effort because of their low toxicity, facile handling, and eco-friendly characteristics. Recently, the development of the C-H activation reaction using organocatalysts has also been studied. We report studies on the oxidative coupling of acridone and nitromethane using a range of radicals. BPAN (tert-butyl(10-phenyl-9-anthryl)nitroxide) was found to be an optimal catalyst for the coupling reaction. It has been considered that in the hydrogen abstraction reaction, the values of the LUMO on the oxygen atom are particularly important. In addition, upon reoxidation to increase catalyst efficiency, the value of the HOMO orbital of the NO-H moiety on the reductant is also important. BPAN was demonstrated to be the optimal radical with regards to all of these values.

Free Research Field

有機合成化学