バイオマスの有効利用を指向した光と金属触媒を用いる炭素－炭素結合切断反応の開発

2016 Fiscal Year Annual Research Report

• Project/Area Number: 16F16340
• Research Institution: Kyoto University
• Principal Investigator: 村上 正浩 京都大学, 工学研究科, 教授 (20174279)
• Co-Investigator(Kenkyū-buntansha): ZHOU WANG 京都大学, 工学研究科, 外国人特別研究員
• Project Period (FY): 2016-10-07 – 2019-03-31
• Keywords: photo redox / copper catalyst / リグニンモデルの分解

Outline of Annual Research Achievements

In the past half year, we developed a photo redox and copper catalytic system for C-C bond cleavage of β-O-4 lignin model compound, giving 3,4-dimethoxybenzaldehyde and 2-methoxyphenyl formate as products in moderate yields. A series of substrates with β-O-4 and β-1 linkage were well-tolerated under standard conditions. The reaction could take place under sunlight, giving the desired products in comparable yields. Some experiments have been carried out to probe the mechanism of this chemistry. Copper catalyst plays an important role in the formation of 2-methoyphenyl formate.

Current Status of Research Progress

2: Research has progressed on the whole more than it was originally planned.

Reason

The research on photo redox and copper catalysis for C-C bond cleavage of lignin model compound have accomplished. We are preparing the manuscript to publish the relevant results. At the same time, we are carrying out a new research topic on photoredox catalyzed C-C bond cleavage of olefin for site-selective alkylation of pyridine.

Strategy for Future Research Activity

For the following fiscal year, we will focus on photoredox catalyzed C-C bond cleavage of olefin for site-selective alkylation of pyridine. We have established the optimal reaction conditions. Now, the substrate scope of this transformation is under investigation. After accomplishing that, we will move to mechanistic study and synthetic application.