These authors contributed equally to this work.
Synthesis of gem-Difluorocyclopropa(e)nes and O-, S-, N-, and P-Difluoromethylated Compounds with TMSCF2Br†
Article first published online: 12 SEP 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 47, pages 12390–12394, November 18, 2013
How to Cite
Li, L., Wang, F., Ni, C. and Hu, J. (2013), Synthesis of gem-Difluorocyclopropa(e)nes and O-, S-, N-, and P-Difluoromethylated Compounds with TMSCF2Br. Angew. Chem. Int. Ed., 52: 12390–12394. doi: 10.1002/anie.201306703
Support of our work by the National Basic Research Program of China (2012CB215500 and 2012CB821600), the National Natural Science Foundation of China (20825209 and 21202189), and the Chinese Academy of Sciences is gratefully acknowledged. TMS=trimethylsilyl.
- Issue published online: 12 NOV 2013
- Article first published online: 12 SEP 2013
- Manuscript Received: 31 JUL 2013
- National Basic Research Program of China. Grant Numbers: 2012CB215500, 2012CB821600
- National Natural Science Foundation of China. Grant Numbers: 20825209, 21202189
- Chinese Academy of Sciences
- synthetic methods
Two-in-one: Me3SiCF2Br is an efficient difluorocarbene source and is compatible with both neutral and aqueous basic conditions. Bromide-ion-initiated [2+1] cycloaddition with alkenes/alkynes and hydroxide ion promoted α-addition with (thio)phenols, (thio)alcohols, sulfinates, heterocyclic amines, and H-phosphine oxides give the corresponding gem-difluorinated compounds with broad functional-group tolerance.