Iron-catalysed aziridination reactions promoted by an ionic liquid

Abstract

A catalytic system based on iron(II) triflate, quinaldic acid and an ionic liquid allows the aziridination of olefins with equimolar amounts of iminoiodinane providing products in good to moderate yields.

The Dinosyl Group: A Powerful Activator for the Regioselective Alcoholysis of Aziridines

“…[11][12][13][14] Although aziridines are close analogs to epoxides, substitution at the nitrogen atom offers an additional handle for tuning their reactivity. Among a large variety of possible activating groups, sulfonyl and in particular tosyl activation is widely used, for good reasons.…”

Transition‐metal‐catalyzed aminations and aziridinations of CH and CC bonds with iminoiodinanes

“…As a continuation of works on Fe(OTf) 2 ‐catalyzed alkene aziridinations with PhINTs, Bolm and co‐workers revealed that 5‐methyl‐2‐pyridinesulfonyliminoiodinane (PhINSO 2 Py) is a suitable nitrene source 35. In this work, reactions of alkenes with PhINSO 2 Py in the presence of quinaldinic acid and ethylmethylimidazolium bis(trifluoromethyl)sulfonyl) amide) (emim BTA) were shown to furnish the aziridine products in 36‐>95% yield ( Scheme ).…”

“…The efficiency of chiral bis(oxazoline) ligands was further demonstrated by their utility in Fe(OTf) 2 ‐catalyzed aziridinations 35. Preliminary studies from the laboratory of Bolm reported that the aziridination of styrene by chiral iron(II) complexes gave the aziridine 8a in moderate yields of 40–75% and with moderate ee values up to 40% (Table 4, entry 12).…”

Iron Catalysis in Synthetic Chemistry

“…Further improvement in yield was obtained by using quinaldic acid in the presence of ionic liquids, such as ethyl methyl imidazolium bis[(trifluoromethyl) sulfonyl]-amide (emim BTA) or LiBTA (Scheme 28) (50).…”