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 multi-arylated 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.

Automated summary

A one-pot site-selective dual metal catalyzed C-H diarylation reaction was developed for the synthesis of multi-arylated thiophene and furan derivatives in high yields up to 92%. The regioselectivity was achieved by sequentially using Ru(II) and Pd(0) catalysts in a single vessel.