Iron-catalyzed aryl–aryl cross-coupling reaction tolerating amides and unprotected quinolinones

Abstract

The iron(III)-catalyzed cross-coupling reaction between functionalized arylcopper reagents and aromatic iodides bearing an amide function or an unprotected quinolinone leads smoothly to polyfunctionalized biphenyls in excellent yields due to an intramolecular chelating effect of the amide group.

2,2,2-Trifluoro-N-(2-iodophenyl)acetamide

“…The title compound was synthesized according to the previously reported procedure (Konfink, et al, 2007).…”

Iron‐Catalyzed Cross‐Coupling Reactions

“…The copper reagent, bearing a triflate protected alcohol, reacts with ethyl 2-iodobenzoate to furnish the biaryl in 62% yield (entry 4). Functionalized quinolinones and secondary amides turned out to react with aryl cuprates, bearing electron-rich or electron-withdrawing subtitutents, with comparatively high yields (entries 6-10) [33].…”

Efficient Sonogashira and A3 coupling reactions catalyzed by biosynthesized magnetic Fe3O4@Ni nanoparticles from Euphorbia maculata extract

“…Therefore, a lot of studies were focused on finding new alternative catalysts for cross‐coupling reactions, which are mainly catalyzed by palladium and nickel based catalysts. In this regard, tremendous attempts have been made to use iron as a catalyst …”

“…In this regard, tremendous attempts have been made to use iron as a catalyst. [81][82][83] Palladium based catalysts, which are extensively used in the Sonogashira cross-coupling reactions, are significantly uneconomical. This restricts their usage in industry.…”