The formal exchange of functional groups in internal positions of two different molecules
is of interest in synthetic chemistry, as a simple retrosynthetic strategy. Here the
formal exchange reaction between internal α-methylene ketones and vinyl ethers, retaining
the original C–O bonds is presented. This process offers a new route for the synthesis
of vinyl ethers in one step from ketones, including 1,3-diketones, under mild reaction
conditions. Besides, the reaction is catalyzed by reusable cheap solids and can be
carried out in flow for 20 days without signs of catalyst depletion. Combined experimental
and computational mechanistic studies unveil the key role of carbonyl–enol equilibria.
Key words
solid catalyst - vinyl ether - ketone - exchange reaction - reaction in flow
