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.
CF Bond Activation of Unactivated Aliphatic Fluorides: Synthesis of Fluoromethyl-3,5-diaryl-2-oxazolidinones by Desymmetrization of 2-Aryl-1,3-difluoropropan-2-ols†
Article first published online: 4 NOV 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 49, pages 12275–12279, December 3, 2012
How to Cite
Haufe, G., Suzuki, S., Yasui, H., Terada, C., Kitayama, T., Shiro, M. and Shibata, N. (2012), CF Bond Activation of Unactivated Aliphatic Fluorides: Synthesis of Fluoromethyl-3,5-diaryl-2-oxazolidinones by Desymmetrization of 2-Aryl-1,3-difluoropropan-2-ols . Angew. Chem. Int. Ed., 51: 12275–12279. doi: 10.1002/anie.201207304
- Issue published online: 28 NOV 2012
- Article first published online: 4 NOV 2012
- Manuscript Received: 10 SEP 2012
- MEXT (Ministry of Education, Culture, Sports, Science and Technology). Grant Number: 24105513
- Deutsche Forschungsgemeinschaft (DFG)
- C-F bond activation;
How to lose fluorine: Biologically relevant oxazolidinones 1 were synthesized through the desymmetrization of unactivated aliphatic difluorides by Si-induced catalytic CF 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 CF bond activation, was also achieved.