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Updated: May 8, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Directed nickel-catalyzed negishi cross coupling of alkyl aziridines
Daniel K Nielsen1, Chung-Yang Dennis Huang, Abigail G Doyle
1Department of Chemistry, Princeton University , Princeton, New Jersey 08544, United States.
Abstract:
Herein we report a nickel-catalyzed C-C bond-forming reaction between simple alkyl aziridines and organozinc reagents. This method represents the first catalytic cross-coupling reaction employing a nonallylic and nonbenzylic Csp(3)-N bond as an electrophile. Key to its success is the use of a new N-protecting group (cinsyl or Cn) bearing an electron-deficient olefin that directs oxidative addition and facilitates reductive elimination. Studies pertinent to elucidation of the mechanism of cross coupling are also presented.
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