Practical Olefin Aziridination with a Broad Substrate Scope

Tung Siu and Andrei K. Yudin*
Department of Chemistry, University of Toronto, 80 St. George St., Toronto, Ontario, Canada M5S 3H6
J. Am. Chem. Soc., 2002, 124 (4), pp 530–531
DOI: 10.1021/ja0172215
Publication Date (Web): January 5, 2002
Copyright © 2002 American Chemical Society
Heterocyclic Compounds (One Hetero Atom)

Abstract

Abstract Image

The present study illustrates the possibility of a rational approach that bypasses the requirement for stoichiometric amounts of toxic oxidants and metal additives (including reagents and catalysts) in organic redox reactions. We describe an aziridination process that delivers a nitrene functionality to olefins from a readily available N-aminophthalimide. Remarkably, both electron-rich and electron-poor olefins are converted to aziridines with high efficiency. The continuum of applied potentials and the heterogeneous nature of reactions at electrode surfaces allow for the electrochemical discrimination of substrates which have similar redox potentials and therefore cannot be selectively reduced or oxidized using soluble reagents. This selectivity is due to the phenomenon of overpotential, the kinetic inhibition of electron transfer on a particular electrode surface.

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History

  • Published In Issue January 30, 2002
  • Received October 3, 2001
    Revised November 27, 2001

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