C[BOND]F Bond Activation of Unactivated Aliphatic Fluorides: Synthesis of Fluoromethyl-3,5-diaryl-2-oxazolidinones by Desymmetrization of 2-Aryl-1,3-difluoropropan-2-ols


  • This study was financially supported in part by Grants-in-Aid for Scientific Research from MEXT (Ministry of Education, Culture, Sports, Science and Technology) (24105513, Project No. 2304: Advanced Molecular Transformation by Organocatalysts) and by the Deutsche Forschungsgemeinschaft (DFG). We thank the Asahi Glass Foundation for partial support.


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How to lose fluorine: Biologically relevant oxazolidinones 1 were synthesized through the desymmetrization of unactivated aliphatic difluorides by Si-induced catalytic C[BOND]F bond-cleavage using BSA/CsF (BSA=bis(trimethylsilyl)acetamide). The direct transformation of 2 with isocyanates into 1 by cascade carbamoylation/cyclization, in which cyclization is induced by Na-assisted C[BOND]F bond activation, was also achieved.