Redox-Neutral α-Sulfenylation of Secondary Amines: Ring-Fused N,S-Acetals

نویسندگان

  • Claire L. Jarvis
  • Matthew T. Richers
  • Martin Breugst
  • K. N. Houk
  • Daniel Seidel
چکیده

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.

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عنوان ژورنال:

دوره 16  شماره 

صفحات  -

تاریخ انتشار 2014