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

[Image: see text] 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 p...

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Autores principales: Jarvis, Claire L., Richers, Matthew T., Breugst, Martin, Houk, K. N., Seidel, Daniel
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4096192/
https://www.ncbi.nlm.nih.gov/pubmed/24927364
http://dx.doi.org/10.1021/ol501509b
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author Jarvis, Claire L.
Richers, Matthew T.
Breugst, Martin
Houk, K. N.
Seidel, Daniel
author_facet Jarvis, Claire L.
Richers, Matthew T.
Breugst, Martin
Houk, K. N.
Seidel, Daniel
author_sort Jarvis, Claire L.
collection PubMed
description [Image: see text] 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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spelling pubmed-40961922015-06-13 Redox-Neutral α-Sulfenylation of Secondary Amines: Ring-Fused N,S-Acetals Jarvis, Claire L. Richers, Matthew T. Breugst, Martin Houk, K. N. Seidel, Daniel Org Lett [Image: see text] 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. American Chemical Society 2014-06-13 2014-07-03 /pmc/articles/PMC4096192/ /pubmed/24927364 http://dx.doi.org/10.1021/ol501509b Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Jarvis, Claire L.
Richers, Matthew T.
Breugst, Martin
Houk, K. N.
Seidel, Daniel
Redox-Neutral α-Sulfenylation of Secondary Amines: Ring-Fused N,S-Acetals
title Redox-Neutral α-Sulfenylation of Secondary Amines: Ring-Fused N,S-Acetals
title_full Redox-Neutral α-Sulfenylation of Secondary Amines: Ring-Fused N,S-Acetals
title_fullStr Redox-Neutral α-Sulfenylation of Secondary Amines: Ring-Fused N,S-Acetals
title_full_unstemmed Redox-Neutral α-Sulfenylation of Secondary Amines: Ring-Fused N,S-Acetals
title_short Redox-Neutral α-Sulfenylation of Secondary Amines: Ring-Fused N,S-Acetals
title_sort redox-neutral α-sulfenylation of secondary amines: ring-fused n,s-acetals
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4096192/
https://www.ncbi.nlm.nih.gov/pubmed/24927364
http://dx.doi.org/10.1021/ol501509b
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AT houkkn redoxneutralasulfenylationofsecondaryaminesringfusednsacetals
AT seideldaniel redoxneutralasulfenylationofsecondaryaminesringfusednsacetals

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