- and -arylation of pyridin-2-ones with diaryliodonium salts: base-dependent orthogonal selectivity under metal-free conditions.

Metal-free - and -arylation reactions of pyridin-2-ones as ambident nucleophiles have been achieved with diaryliodonium salts on the basis of base-dependent chemoselectivity. In the presence of ,-diethylaniline in fluorobenzene, pyridin-2-ones were very selectively converted to -arylated products in high yields. On the other hand, the -arylation reactions smoothly proceeded with the use of quinoline in chlorobenzene, leading to high yields and selectivities.