Synthesis of arylated anthraquinones by site-selective Suzuki–Miyaura reactions of the bis(triflates) of 1,3-di(hydroxy)anthraquinones

Arylated anthraquinones were prepared by Suzuki–Miyaura reactions of the bis(triflates) of various 1,3-(dihydroxy)anthraquinones. While the reactions of the bis(triflates) of parent 1,3-(dihydroxy)anthraquinone and of 2-chloro-1,3-di(hydroxy)anthraquinone proceeded with very good site-selectivity, the corresponding reactions of the bis(triflate) of 2-fluoro-1,3-diarylanthraquinones were not site-selective, which was explained based on the π-donating effect of the fluorine atom.