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

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

doi:10.1021/ol501509b

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

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

Research output: Contribution to journal › Article › peer-review

64 Scopus citations

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.

Original language	English
Pages (from-to)	3556-3559
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	13
DOIs	https://doi.org/10.1021/ol501509b
State	Published - 3 Jul 2014
Externally published	Yes

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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.",

author = "Jarvis, {Claire L.} and Richers, {Matthew T.} and Martin Breugst and Houk, {K. N.} and Daniel Seidel",

year = "2014",

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AU - Jarvis, Claire L.

AU - Richers, Matthew T.

AU - Breugst, Martin

AU - Houk, K. N.

AU - Seidel, Daniel

PY - 2014/7/3

Y1 - 2014/7/3

N2 - 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.

AB - 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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Redox-neutral α-sulfenylation of secondary amines: Ring-fused N,S-acetals

Abstract

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