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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Diboron-Enabled Copper-Catalyzed Modular Synthesis of Difluoromethylated and Perfluoroalkylated Oxazolines
Ling Xiong1, Jiaming Chen1, Jiaming Li1
1School of Chemistry and Chemical Engineering, Nanchang University, Nanchang, Jiangxi330031, China.
Abstract:
A diboron-enabled copper-catalyzed modular synthesis of difluoromethylated and perfluoroalkylated oxazolines has been developed through the radical cyclization of N-allylamides with perfluoroalkyl iodides (IRf). This protocol provides efficient access to diverse difluoromethylated and perfluoroalkylated oxazolines under mild conditions via radical addition and subsequent intramolecular cyclization. The reaction exhibits a broad substrate scope and excellent functional group tolerance across aryl, heteroaryl, and aliphatic N-allylamides, accommodating various perfluoroalkyl chains. Gram-scale synthesis and downstream transformations further demonstrated its synthetic utility. This method offers a practical platform for constructing valuable fluorinated oxazolines in medicinal chemistry.
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