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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Isoquinolinium Photooxidant for Arene C-H Amination
Taku Wakabayashi1, Yaoyue Liu1, Itziar Guerrero1
1School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore 637371, Singapore.
A new photocatalytic method uses an isoquinolinium photooxidant for efficient arene C-H amination. This system enables single-electron-transfer oxidation of inert arenes, broadening its synthetic utility.
Area of Science:
- Organic Chemistry
- Photocatalysis
- C-H Functionalization
Background:
- Arene C-H amination is a crucial transformation in organic synthesis.
- Developing efficient photocatalytic systems for C-H functionalization remains a significant challenge.
Purpose of the Study:
- To report a novel photocatalytic system for arene C-H amination.
- To utilize an isoquinolinium photooxidant for efficient oxidation of arenes.
Main Methods:
- Employing an isoquinoline precatalyst (IQ1) that undergoes in situ protonation.
- Utilizing the protonated isoquinolinium (IQ1•H+) as a potent photooxidant with a high excited-state reduction potential.
- Optimizing reaction conditions for arene C-H amination.
Main Results:
- The isoquinolinium photooxidant (IQ1•H+) demonstrated a high excited-state reduction potential of +2.33 V vs SCE.
- The system enabled efficient single-electron-transfer oxidation of inert arenes.
- The optimized reaction showed a broad scope, including neutral arenes and pharmaceutical molecules containing azoles and pyridines.
Conclusions:
- A potent photocatalytic system for arene C-H amination has been developed.
- The isoquinolinium photooxidant is effective for single-electron-transfer oxidation of arenes.
- The method offers a versatile approach for functionalizing diverse aromatic compounds.
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