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Updated: Jun 19, 2025
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Synthesis and application of well-defined [Ph4P]+[Cu(CF2CF3)2]- complex as a versatile pentafluoroethylating reagent
Tao Dong1, Qilong Shen2, Gavin Chit Tsui1,3
1Department of Chemistry, The Chinese University of Hong Kong Shatin, New Territories Hong Kong SAR China gctsui@cuhk.edu.hk.
A novel organocuprate reagent enables efficient pentafluoroethylation across various organic substrates. This single reagent facilitates the formation of diverse carbon-CF2CF3 bonds, simplifying synthetic pathways.
Area of Science:
- Organometallic Chemistry
- Fluorine Chemistry
Background:
- Organocuprates are valuable synthetic intermediates.
- Pentafluoroethylation is a key transformation in organic synthesis.
Purpose of the Study:
- To develop a new, versatile pentafluoroethylating reagent.
- To explore the reactivity of the novel organocuprate.
Main Methods:
- Preparation of the bispentafluoroethylated organocuprate, [Ph4P]+[Cu(CF2CF3)2]-.
- Testing the reagent's reactivity with various organic functional groups and (hetero)arenes.
Main Results:
- The organocuprate demonstrated broad reactivity towards carboxylic acids, diazonium salts, organic halides, boronic esters, terminal alkynes, and (hetero)arenes.
- Successful construction of C(sp3)-, C(sp2)-, and C(sp)-CF2CF3 bonds was achieved.
Conclusions:
- The new organocuprate is a versatile reagent for pentafluoroethylation.
- A single reagent can be used to form various carbon-CF2CF3 bonds.
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