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Prof. Dr. Günter Haufe, Satoru Suzuki, Hiroyuki Yasui, Chisato Terada, Takashi Kitayama, Dr. Motoo Shiro and Prof. Dr. Norio Shibata 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 Angewandte Chemie International Edition 51

Article first published online: 4 NOV 2012 | DOI: 10.1002/anie.201207304

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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.

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