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Published on: November 30, 2022
Suzuki coupling of oxazoles
Emmanuel Ferrer Flegeau1, Matthew E Popkin, Michael F Greaney
1University of Edinburgh, School of Chemistry, Joseph Black Building, King's Buildings, West Mains Road, Edinburgh EH9 3JJ, U.K.
This study introduces a new Suzuki coupling protocol for functionalizing oxazoles at the 2- and 4-positions. The method efficiently synthesizes diverse aryl- and heteroaryl-substituted oxazoles and novel dioxazoles.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Heterocyclic Chemistry
Background:
- Oxazole derivatives are important scaffolds in medicinal chemistry and materials science.
- Efficient methods for functionalizing oxazoles, particularly at the 2- and 4-positions, are crucial for expanding their synthetic utility.
Purpose of the Study:
- To develop a versatile protocol for the regioselective functionalization of oxazoles at the 2- and 4-positions.
- To explore the application of this methodology in synthesizing novel homo- and heterodimeric dioxazoles.
Main Methods:
- Utilized Suzuki coupling reactions for oxazole functionalization.
- Employed microwave-assisted synthesis for rapid coupling reactions.
- Investigated the use of 2-aryl-4-trifloyloxazoles and 4-aryl-2-chlorooxazoles as key substrates.
Main Results:
- Achieved good to excellent yields for the Suzuki coupling of various aryl and heteroaryl boronic acids with oxazole precursors.
- Demonstrated the effectiveness of the protocol with both triflate and chloride leaving groups.
- Successfully synthesized a novel class of 4,4-linked dioxazoles.
Conclusions:
- The described Suzuki coupling protocol offers an efficient and versatile route to functionalized oxazoles.
- The methodology is applicable to the synthesis of complex heterocyclic structures, including novel dioxazoles.
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