This study was supported financially in part by Grants-in-Aid for Scientific Research (B; No. 21390030, JSPS; 22106515, JSPS). We are grateful to the Central Glass Co., Ltd. for support.
Inherent Oxygen Preference in Enolate Monofluoromethylation and a Synthetic Entry to Monofluoromethyl Ethers†
Article first published online: 23 DEC 2010
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 50, Issue 8, pages 1885–1889, February 18, 2011
How to Cite
Nomura, Y., Tokunaga, E. and Shibata, N. (2011), Inherent Oxygen Preference in Enolate Monofluoromethylation and a Synthetic Entry to Monofluoromethyl Ethers. Angew. Chem. Int. Ed., 50: 1885–1889. doi: 10.1002/anie.201006218
- Issue published online: 16 FEB 2011
- Article first published online: 23 DEC 2010
- Manuscript Received: 4 OCT 2010
- CO bond formation;
Expect the unexpected: The self-stable salts 1, X=OTf, PF6, x=2, y=1, developed for electrophilic monofluoromethylation showed inherent selectivity for the O-alkylation of enolates, thus providing access to monofluoromethyl ethers, which are difficult to obtain by the direct electrophilic fluoromethylation of alcohols. Salt 1, X=BF4, x=0, y=3, in contrast leads to C-alkylated products.