Skip to main content
eScholarship
Open Access Publications from the University of California

Redox-neutral α-sulfenylation of secondary amines: ring-fused N,S-acetals.

  • Author(s): Jarvis, Claire L
  • Richers, Matthew T
  • Breugst, Martin
  • Houk, KN
  • Seidel, Daniel
  • et al.

Published Web Location

https://doi.org/10.1021/ol501509b
Abstract

Secondary amines react with thiosalicylaldehydes in the presence of catalytic amounts of acetic acid to generate ring-fused N,S-acetals in redox-neutral fashion. A broad range of amines undergo α-sulfenylation, including challenging substrates such morpholine, thiomorpholine, and piperazines. Computational studies employing density functional theory indicate that acetic acid reduces the energy barriers of two separate steps, both of which involve proton transfer.

Many UC-authored scholarly publications are freely available on this site because of the UC's open access policies. Let us know how this access is important for you.

Main Content
Current View