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A Protocol for Safe Lithiation Reactions Using Organolithium Reagents
Published on: November 12, 2016
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Dilithium Amides as a Modular Bis-Anionic Ligand Platform for Iron-Catalyzed Cross-Coupling
Peter G N Neate1, Bufan Zhang1, Jessica Conforti1
1Department of Chemistry, University of Rochester, Rochester, New York 14627, United States.
Organic Letters
|July 26, 2021
Summary
New dilithium amide ligands enable versatile iron-catalyzed cross-coupling reactions. This general ligand system efficiently couples alkyl and aryl Grignard reagents with various electrophiles, simplifying complex organic synthesis.
Area of Science:
- Organometallic Chemistry
- Organic Synthesis
Background:
- Iron catalysis offers a sustainable alternative to precious metal catalysts.
- Kumada-Tamao-Corriu cross-coupling reactions are vital for C-C bond formation.
- Ligand design is crucial for controlling reactivity and selectivity in catalysis.
Purpose of the Study:
- To develop a general and bespoke ligand for iron-catalyzed Kumada-Tamao-Corriu cross-coupling reactions.
- To enable the coupling of diverse Grignard reagents with various electrophiles using a single catalytic system.
Main Methods:
- Design and synthesis of novel dilithium amide ligands.
- Iron-catalyzed cross-coupling reactions involving alkyl and aryl Grignard reagents.
- Optimization of reaction conditions for broad substrate scope.
Main Results:
- Dilithium amides demonstrated efficacy as general ligands for iron catalysis.
- Successful cross-coupling of alkyl Grignard reagents with sp2-hybridized electrophiles.
- Successful cross-coupling of aryl Grignard reagents with sp3-hybridized electrophiles.
- The catalytic system remained effective across diverse coupling reactions without significant protocol modification.
Conclusions:
- Dilithium amides represent a versatile ligand class for iron-catalyzed cross-coupling.
- The developed system offers a simple and broadly applicable method for C-C bond formation.
- This work advances the utility of iron catalysis in organic synthesis.
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