Redox-Neutral α-Sulfenylation of Secondary Amines: Ring-Fused N , S -Acetals
2014; American Chemical Society; Volume: 16; Issue: 13 Linguagem: Inglês
10.1021/ol501509b
ISSN1523-7060
AutoresClaire L. Jarvis, Matthew T. Richers, Martin Breugst, K. N. Houk, Daniel Seidel,
Tópico(s)Synthesis and Catalytic Reactions
ResumoSecondary 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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