We based our previous work on a 1994 paper from Phil Fuchs' laboratory, which only reported one successful reaction, which was with benzaldehyde as the electrophile. They felt that the low nucleophilicity of the anion was the reason for there not being more positive results. They used potassium t-butoxide and THF, and we have twice attempted to duplicate their conditions, but in our hands, we found that reflux was necessary. The first yield was modest but acceptable (55%). I have not found any other HWE examples in the literature. We would like to make one or two from heteroaromatic aldehydes, possibly with a quinoline or an aromatic/heteroaromatic bearing a nitro group. Should we try LiCl/DBU/acetonitrile, which is our standard method? Should we try a third base?
EDT
The nucleophile is the anion of (EtO)2P(O)CH2S(O)2CF3.