Styrene Aziridination by Iron(IV) Nitrides.

Angewandte Chemie (International ed. in English)

PubMedID: 26179563

Muñoz SB, Lee WT, Dickie DA, Scepaniak JJ, Subedi D, Pink M, Johnson MD, Smith JM. Styrene Aziridination by Iron(IV) Nitrides. Angew Chem Int Ed Engl. 2015;.
Thermolysis of the iron(IV) nitride complex [PhB(tBuIm)3 Fe?N] with styrene leads to formation of the high-spin iron(II) aziridino complex [PhB(tBuIm)3 Fe-N(CH2 CHPh)]. Similar aziridination occurs with both electron-rich and electron-poor styrenes, while bulky styrenes hinder the reaction. The aziridino complex [PhB(tBuIm)3 Fe-N(CH2 CHPh)] acts as a nitride synthon, reacting with electron-poor styrenes to generate their corresponding aziridino complexes, that is, aziridine cross-metathesis. Reaction of [PhB(tBuIm)3 Fe-N(CH2 CHPh)] with Me3 SiCl releases the N-functionalized aziridine Me3 SiN(CH2 CHPh) while simultaneously generating [PhB(tBuIm)3 FeCl]. This closes a synthetic cycle for styrene azirdination by a nitride complex. While the less hindered iron(IV) nitride complex [PhB(MesIm)3 Fe?N] reacts with styrenes below room temperature, only bulky styrenes lead to tractable aziridino products.