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Updated: Aug 21, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Cu(I) beta-diketiminates for alkene aziridination: reversible Cu-arene binding and catalytic nitrene transfer from
Latasha D Amisial1, Xuliang Dai, R Adam Kinney
1Department of Chemistry, Box 571227, Georgetown University, Washington, DC 20057, USA.
Abstract:
beta-Diketiminato Cu(I)-lutidine complexes [RMeNN]Cu(2,4-lutidine) (R = Me (4a), (i)Pr (4b)) were prepared in high yield from Tl[RMeNN] and [CuBr(2,4-lutidine)(2)](2). Both 4a and 4b reversibly dissociate lutidine base in toluene to give [RMeNN]Cu(toluene) solvento complexes. A related base-free dicopper species [[Me(2)NN]Cu](2) (6) bridged via eta(2)-binding of opposing N-aryl rings could be isolated by the addition of Tl[Me(2)NN] to CuBr. The lutidine precursors serve as precatalysts for the aziridination of alkenes with PhI=NTs. Styrene, beta-methylstyrene, and cyclooctene gave the highest yields (59-96%) with a low olefin to PhI=NTs ratio (3:1) and 5 mol % catalyst loading.
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