Styrene Aziridination by Iron(IV) Nitrides1. (14th July 2015)

• Record Type: Journal Article
• Authors: Muñoz, Salvador B.; Lee, Wei‐Tsung; Dickie, Diane A.; Scepaniak, Jeremiah J.; Subedi, Deepak; Pink, Maren; Johnson, Michael D.; Smith, Jeremy M.
• Is Part Of: Angewandte Chemie. Volume 127:Number 36(2015)
• Page Start: 10746
• Page End: 10749
• Publication Date: 2015-07-14
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201503773
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Thermolysis of the iron(IV) nitride complex [PhB(<italic>t</italic>BuIm)₃FeN] with styrene leads to formation of the high‐spin iron(II) aziridino complex [PhB(<italic>t</italic>BuIm)₃Fe‐N(CH₂CHPh)]. Similar aziridination occurs with both electron‐rich and electron‐poor styrenes, while bulky styrenes hinder the reaction. The aziridino complex [PhB(<italic>t</italic>BuIm)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(<italic>t</italic>BuIm)₃Fe‐N(CH₂CHPh)] with Me₃SiCl releases the N‐functionalized aziridine Me₃SiN(CH₂CHPh) while simultaneously generating [PhB(<italic>t</italic>BuIm)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.</p> </abstract>