Catalyst-free regioselective hydroxyfluorination and aminofluorination of α,β-unsaturated ketones?

Organic & Biomolecular Chemistry Pub Date: 2019-04-16 DOI: 10.1039/C9OB00467J

Abstract

The catalyst-free direct regioselective α-fluoro-β-hydroxylation and α-fluoro-β-amidation of α,β-unsaturated ketones has been developed. Various α,β-unsaturated ketones react with Selectfluor in water and acetonitrile to give α-fluorohydrins and α-fluoroamides respectively with moderate to good yields. The mechanistic studies revealed the possibility of a radical based pathway.

Graphical abstract: Catalyst-free regioselective hydroxyfluorination and aminofluorination of α,β-unsaturated ketones
Recommended Literature