We previously reported the synthesis of a Cr(III) tetracarbene complex, which has proven to be an effective catalyst for C2 + N1 aziridination of aryl azides and aliphatic alkenes. This catalyst is particularly effective at low alkene loadings compared to our previous iron aziridination catalysts. The observed increase in reactivity with lower alkene loadings has been attributed to the presence of axial chloride ligands which we propose hinder formation of a competing tetrazene complex. The chromium catalyst shows a higher tolerance for protic functional groups, such as alcohols, than previously reported catalysts, which is critical for the synthesis of pharmaceutical intermediates. Finally, to our knowledge, this represents the first report of aziridination catalysis on chromium.

Synthesis of aziridines at low alkene loadings catalyzed by a chromium(III) tetracarbene complex

253rd National Meeting (2017)

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