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

Hamad H. Al Mamari, Uroš Grošelj, Franc Požgan, Helena Brodnik*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3138-3151
Number of pages14
JournalJournal of Organic Chemistry
Volume86
Issue number4
DOIs
Publication statusPublished - Feb 19 2021
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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