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A counteranion triggered arylation strategy using diaryliodonium fluorides.
1Department of Chemistry , University of Cambridge , Lensfield Road , Cambridge CB2 1EW , UK . Email: mjg32@cam.ac.uk ; Tel: +44 1223 336318.
Chemical Science
|March 16, 2018
Summary
A new transition metal-free method uses diaryliodonium fluorides for O-arylation. The fluoride anion activates phenolic O-H bonds under mild conditions, enabling broad substrate compatibility and potential for C-H functionalization.
Area of Science:
- Organic Chemistry
- Synthetic Methodology
Background:
- Transition metal catalysis is prevalent in C-O bond formation.
- Developing metal-free alternatives is crucial for sustainable synthesis.
Purpose of the Study:
- To develop a novel, mild, and transition metal-free O-arylation strategy.
- To utilize diaryliodonium salts with a unique counteranion activation mechanism.
Main Methods:
- Employing diaryliodonium fluorides as arylating agents.
- Investigating the role of the fluoride counteranion in activating phenolic O-H bonds.
- Exploring the reaction scope with diverse phenols and diaryliodonium salts.
Main Results:
- Achieved efficient electrophilic O-arylation under mild, metal-free conditions.
- Demonstrated broad substrate scope, tolerating various functional groups.
- Showcased compatibility with latent carbon nucleophiles, suggesting broader applicability.
Conclusions:
- A novel diaryliodonium fluoride-mediated O-arylation strategy has been established.
- This method offers a mild, efficient, and metal-free route for C-O bond formation.
- The findings open avenues for further development in C-H functionalization strategies.
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