Mj. Shiao et al., SYNTHESIS OF 4-ARYLPYRIDINES CONTAINING ELECTRON-WITHDRAWING GROUPS ON THE BENZENE-RING, Journal of the Chinese Chemical Society, 40(2), 1993, pp. 175-179
4-Arylpyridines 5 that contain electron-withdrawing groups such as nit
rile, methyl ester, fluoride, and trifluoromethyl on the benzene ring
were synthesized in moderate yields (29-63%) by reaction of mixed copp
er, zinc aryl organometallics 1 with various 1-(ethoxycarbonyl)pyridin
ium chlorides 2 followed by o-chloranil oxidization under reflux in to
luene.