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Styrene Aziridination by Iron(IV) Nitrides.

ABSTRACT: Thermolysis of the iron(IV) nitride complex [PhB(tBuIm)3Fe?N] with styrene leads to formation of the high-spin iron(II) aziridino complex [PhB(tBuIm)3Fe-N(CH2CHPh)]. Similar aziridination occurs with both electron-rich and electron-poor styrenes, while bulky styrenes hinder the reaction. The aziridino complex [PhB(tBuIm)3Fe-N(CH2CHPh)] 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)3Fe-N(CH2CHPh)] with Me3SiCl releases the N-functionalized aziridine Me3SiN(CH2CHPh) while simultaneously generating [PhB(tBuIm)3FeCl]. This closes a synthetic cycle for styrene azirdination by a nitride complex. While the less hindered iron(IV) nitride complex [PhB(MesIm)3Fe?N] reacts with styrenes below room temperature, only bulky styrenes lead to tractable aziridino products.

SUBMITTER: Munoz SB

PROVIDER: S-EPMC4625910 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

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Styrene Aziridination by Iron(IV) Nitrides.

Muñoz Salvador B SB Lee Wei-Tsung WT Dickie Diane A DA Scepaniak Jeremiah J JJ Subedi Deepak D Pink Maren M Johnson Michael D MD Smith Jeremy M JM

Angewandte Chemie (International ed. in English) 20150715 36

Thermolysis of the iron(IV) nitride complex [PhB(tBuIm)3Fe≡N] with styrene leads to formation of the high-spin iron(II) aziridino complex [PhB(tBuIm)3Fe-N(CH2CHPh)]. Similar aziridination occurs with both electron-rich and electron-poor styrenes, while bulky styrenes hinder the reaction. The aziridino complex [PhB(tBuIm)3Fe-N(CH2CHPh)] acts as a nitride synthon, reacting with electron-poor styrenes to generate their corresponding aziridino complexes, that is, aziridine cross-metathesis. Reaction ...[more]

PMID: 26179563

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