Dual Catalysis with Photoredox Catalysts for Organic Transformations Mediated by Single-Electron Transfer Processes

2017 Fiscal Year Final Research Report

• Project/Area Number: 16K17865
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: The University of Tokyo
• Principal Investigator: Yoo Woo-Jin 東京大学, 大学院理学系研究科(理学部), 特任助教 (70626077)
• Project Period (FY): 2016-04-01 – 2018-03-31
• Keywords: carbon dioxide / multi-component coupling / copper / flourine / lactone

Outline of Final Research Achievements

I investigated the synthesis of lactones from carbon dioxide and readily available starting materials by two different strategies. The first approach involved combining C-H activation (C-H silylation) chemistry with copper-catalyzed carboxylation reaction to convert benzyl alcohols to phthalides. The second approach involved a sequential trans-hydroalumination and copper-catalyzed carboxylation reaction to convert propargyl alcohols into butenolides.

Finally, I have interest in developing multi-component coupling reactions with carbon dioxide to make complex organic molecules. I found that 1-aryl-2,2-difluoroalkenes can undergo fluorocarboxylation with carbon dioxide and cesium fluoride to provide trifluoromethyl carboxylic acids in good yields.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

Various strategies of utilizing carbon dioxide as a sustainable source of a carbon feedstock to synthesize various value-added organic substrates have been discovered through our studies, and it is anticipated that our finding can be used to sustainably synthesis other complex organic molecules.