Regioselective Ru(II)/Pd(0) Dual Catalysis: One-Pot C–H Diarylation of Five-Membered Heterocyclic Derivatives

Herein, we report a one-pot site-selective dual metal catalyzed C–H diarylation reaction for the synthesis of multiarylated thiophene and furan derivatives in yields up to 92%. The regioselectivity of the developed methodology was achieved with the sequential use of two metal catalysts within a single vessel, starting with a Ru(II)-catalyzed C3 arylation assisted by an azine directing group, followed by a Pd(0)-catalyzed C–H functionalization on the C5-position of the five-membered heterocycle. Furthermore, the kinetic studies support that the position of the nitrogen atom within the azine moiety exhibits an evident effect on the efficiency of the ruthenium-catalyzed arylation step.

Read article: J. Org. Chem., 2021, 86, 4, 3138