Issue 6, 2014

Selective monofluorination of active methylene compounds: the important role of ZnCl2 in inhibiting overfluorination

Abstract

In the presence of zinc chloride (ZnCl2), active methylene compounds can be selectively monofluorinated at room temperature, and the undesired overfluorination (gem-difluorination) can be significantly diminished. The mechanistic study shows that ZnCl2 plays an important role in selective monofluorination through its interaction with a Brønsted base to control the deprotonation of the starting methylene compounds over the corresponding monofluorinated products.

Graphical abstract: Selective monofluorination of active methylene compounds: the important role of ZnCl2 in inhibiting overfluorination

Supplementary files

Article information

Article type
Research Article
Submitted
25 3 2014
Accepted
25 4 2014
First published
28 4 2014

Org. Chem. Front., 2014,1, 625-629

Author version available

Selective monofluorination of active methylene compounds: the important role of ZnCl2 in inhibiting overfluorination

F. Jiang, Y. Zhao and J. Hu, Org. Chem. Front., 2014, 1, 625 DOI: 10.1039/C4QO00090K

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