Development of photoacid organocatalysts

• Project/Area Number: 26620080
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Kyoto University
• Principal Investigator: Taichi Kano 京都大学, 理学研究科, 准教授 (40372560)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Project Status: Completed (Fiscal Year 2016)
• Budget Amount: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000); Fiscal Year 2016: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000); Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
• Keywords: 酸塩基複合触媒 / ブレンステッド酸触媒

Outline of Final Research Achievements

A binaphthyl-based secondary amine catalyst having hydroxy group as a bifunctional organocatalyst was synthesized and applied to the reaction between aliphatic aldehyde and nitrosobenzene. 2-Naphthol is a weak organic acid and its acidity is known to be increased by UV irradiation. The newly synthesized bifunctional catalyst, which has 2-naphthol moiety, was found to promote both aminoxylation and hydroxyamination. Under UV irradiation, the product ratio of aminoxylation and hydroxyamination changed. This result suggested that the acidity of the bifunctional catalyst was increased by UV irradiation, since the aminoxylation requires a relatively strong acid catalyst.