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Updated: May 29, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
Published on: June 20, 2014
Catalytic migratory oxidative coupling of nitrones through an outer-sphere C(sp3)-H activation process
Shogo Hashizume1, Kounosuke Oisaki, Motomu Kanai
1Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Tokyo 113-0033, Japan.
This study demonstrates copper(I)-catalyzed outer-sphere redox catalysis for C-H activation, enabling selective C-C bond formation in coupling reactions. The findings pave the way for new catalytic methods in organic synthesis.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Chemistry
Background:
- Outer-sphere redox catalysis is crucial for C-H activation reactions.
- C-H activation is a significant area of interest in modern organic chemistry.
Purpose of the Study:
- To describe a copper(I)-catalyzed oxidative coupling reaction.
- To showcase predictable site-selective C-C bond formation using nitrones and ethers/amines.
Main Methods:
- Utilized copper(I) catalysis for oxidative coupling.
- Investigated C-H bond activation and C-N double bond migration.
- Conducted mechanistic studies to identify key intermediates.
Main Results:
- Achieved predictable site-selective C-C bond formation.
- Demonstrated successful coupling between nitrones and various ethers or amines.
- Identified oxonium/iminium cation species as key reaction intermediates.
Conclusions:
- Outer-sphere redox catalysis provides an efficient route for C-H activation.
- The mechanistic insights gained can guide future developments in catalysis.
- This work expands the scope of catalytic C-C bond formation.
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