2023 Fiscal Year Research-status Report
Development of Indigos as Red-Light Photoredox Catalysts
| Project/Area Number |
23K13734
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| Research Institution | Hokkaido University |
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Principal Investigator |
HUANG CHUNG・YANG 北海道大学, 化学反応創成研究拠点, 准教授 (90956153)
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| Project Period (FY) |
2023-04-01 – 2026-03-31
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| Keywords | indigo / photoredox / organic synthesis / metal catalysis |
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| Outline of Annual Research Achievements |
Synthetic methods have been developed to prepare several prototype indigo molecules, and these compounds show photoredox activity using irradiation wavelengths longer than blue light. These compounds also show catalytic reactivity in several test photoredox reactions. Unexpectedly, during these studies, we discovered two related photoredox methodologies in the area of C-F activation. First, selective hydrodefluorination of trifluoromethylarenes has been optimized using N-heterocyclic carbene boranes as the hydrogen atom transfer reagent. Second, a copper-catalyzed photoredox C-O coupling with trifluoromethylarenes has been developed.
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| Current Status of Research Progress |
Current Status of Research Progress
2: Research has progressed on the whole more than it was originally planned.
Reason
In addition to the original plan, we have discovered two related photoredox methodologies in the area of C-F activation. These new directions are currently being actively pursued, where substrate scope evaluation and mechanistic studies will be complete in the near future. Publications can then be expected within this FY. The implications of these novel synthetic method are in C-F functionalization as well as photoredox reactivity.
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| Strategy for Future Research Activity |
We will continue to explore indigo-derived photoredox catalysts. The first goal is to build structures that extend the absorption to red-light region while maintaining photoredox activity. Second, we will explore different types of transformations where this class of catalyst can play a decisive role. Additionally, as a related direction, the utility of these compounds as imaging and therapeutic agents for biomedical research will be investigated.
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| Causes of Carryover |
In the past FY, due to the necessity to first utilize funds from Hokkaido University and WPI-ICReDD, not much KAKENHI has been consumed. In this FY, we will begin to employ more from this KAKENHI funds for this research project.
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