In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Importance of Two-Electron Processes in Fe-Catalyzed Aryl-(hetero)aryl Cross-Couplings: Evidence of Fe0/Fe(II) Couple Implication, published in 2021-10-11, which mentions a compound: 1008-89-5, mainly applied to iron catalyzed aryl heteroaryl halide coupling reaction Grignard reagent; biaryl preparation; kinetics coupling reaction Grignard reagent aryl halide iron catalyst, Related Products of 1008-89-5.
Two drastically distinct mechanisms can be involved in aryl-(hetero)aryl Fe-mediated cross-couplings between Grignard reagents and organic halides, depending on the nature of the latter. (Hetero)aryl electrophiles, which easily undergo 1-electron reduction, can be involved in a Fe(II)/Fe(III) coupling sequence featuring an in situ generated organoiron(II) species, akin to their aliphatic analogs. However, less easily reduced substrates can be activated by transient Fe0 species formed by the reduction of the precatalyst. In this case, the coupling mechanism relies on two-electron elementary steps involving the Fe0/Fe(II) redox couple and proceeds by an oxidative addition/reductive elimination sequence. Hammett anal. shows that both those elementary steps are faster for electrophiles substituted by electron-withdrawing groups. The two mechanisms discussed herein can be involved concomitantly for electrophiles displaying an average oxidative power. Attesting to the feasibility of the aforementioned bielectronic mechanism, high-spin organoiron(II) intermediates formed by two-electron oxidative addition onto (hetero)aryl halides in catalytically relevant conditions were also characterized for the 1st time. Those results are sustained by paramagnetic 1H NMR, kinetics monitoring, and d. functional theory (DFT) calculations
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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles