Electrochemical Imination of Sulfoxides Using N-Aminophthalimide

Tung Siu and Andrei K. Yudin*
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada
Org. Lett., 2002, 4 (11), pp 1839–1842
DOI: 10.1021/ol0257530
Publication Date (Web): May 7, 2002
Copyright © 2002 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, ayudin@chem.utoronto.ca

Abstract

Abstract Image

A novel electrochemical sulfoxide imination process is described. Our approach starts with a highly selective nitrene transfer from N-aminophthalimide to a variety of sulfoxides. This oxidative treatment is followed by reductive N−N bond cleavage under the controlled current conditions, which leads to a range of parent NH sulfoximines. In addition to solving the challenging problem of removing the N-phthalimido group, the overall process avoids the use of toxic oxidants and metal additives.

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History

  • Published In Issue May 30, 2002
  • Received February 20, 2002
    Revised April 22, 2002

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