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

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 ?-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.

SUBMITTER: Jarvis CL

PROVIDER: S-EPMC4096192 | biostudies-literature | 2014 Jul

REPOSITORIES: biostudies-literature

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

Jarvis Claire L CL Richers Matthew T MT Breugst Martin M Houk K N KN Seidel Daniel D

Organic letters 20140613 13

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. ...[more]

PMID: 24927364

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