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Carbon-Based Weakly Coordinating Anions: Molecular Design, Synthesis and Applications
Leif Kelling1, Julian Eßer1, Daniel Knyszek1
1Inorganic Chemistry II, Ruhr-University Bochum, Universitätsstraße 150, 44801, Bochum, Germany.
Angewandte Chemie (International Ed. in English)
|June 15, 2024
Summary
This study explores carbanions as weakly coordinating anions (WCA), synthesizing a stable allyl anion. This novel WCA stabilizes reactive cations and serves as a reagent for hydride abstraction.
Area of Science:
- Organometallic Chemistry
- Anion Design
- Synthetic Chemistry
Background:
- Carbanions are typically reactive and used as metalation reagents.
- Weakly coordinating anions (WCA) are crucial for stabilizing reactive cations.
- Carbanions have been largely overlooked in WCA design.
Purpose of the Study:
- To evaluate the potential of substituted carbanions as WCAs.
- To synthesize and characterize novel carbanion-based WCAs.
- To demonstrate the utility of these WCAs in stabilizing reactive cations.
Main Methods:
- Computational evaluation of carbanion stability and coordinating ability.
- Synthesis of a water- and air-stable allyl anion (1) with triflyl and ArF groups.
- Characterization using single crystal X-ray crystallography and NMR spectroscopy.
Main Results:
- The synthesized allyl anion (1) exhibits weak coordination to cations.
- Anion 1 successfully stabilized reactive group 14 and 15 cations.
- Crystallization of a phosphenium cation and the first all-carbon salt with a non-aromatic carbanion was achieved.
- The all-carbon salt demonstrated utility as a hydride abstraction reagent.
Conclusions:
- Carbanions possess untapped potential as versatile WCAs.
- The developed carbanion-based WCAs are stable and synthetically accessible.
- These WCAs open new avenues for stabilizing reactive species and facilitating chemical transformations.
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