C-Sulfonylation of 4-Alkylpyridines: Formal Picolyl C–H Activation via Alkylidene Dihydropyridine Intermediates

[Image: see text] 4-Picoline derivatives are converted to the corresponding aryl picolyl sulfones upon treatment with aryl sulfonyl chlorides and Et(3)N in the presence of catalytic DMAP. The reaction proceeds smoothly for a variety of alkyl and aryl picolines using a range of aryl sulfonyl chloride...

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Autores principales: Tun, Soe L., Shivers, Grant N., Pigge, F. Christopher
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10028608/
https://www.ncbi.nlm.nih.gov/pubmed/36848377
http://dx.doi.org/10.1021/acs.joc.3c00017
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author Tun, Soe L.
Shivers, Grant N.
Pigge, F. Christopher
author_facet Tun, Soe L.
Shivers, Grant N.
Pigge, F. Christopher
author_sort Tun, Soe L.
collection PubMed
description [Image: see text] 4-Picoline derivatives are converted to the corresponding aryl picolyl sulfones upon treatment with aryl sulfonyl chlorides and Et(3)N in the presence of catalytic DMAP. The reaction proceeds smoothly for a variety of alkyl and aryl picolines using a range of aryl sulfonyl chlorides. The reaction is believed to involve N-sulfonyl 4-alkylidene dihydropyridine intermediates and results in formal sulfonylation of unactivated picolyl C–H bonds.
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spelling pubmed-100286082023-03-22 C-Sulfonylation of 4-Alkylpyridines: Formal Picolyl C–H Activation via Alkylidene Dihydropyridine Intermediates Tun, Soe L. Shivers, Grant N. Pigge, F. Christopher J Org Chem [Image: see text] 4-Picoline derivatives are converted to the corresponding aryl picolyl sulfones upon treatment with aryl sulfonyl chlorides and Et(3)N in the presence of catalytic DMAP. The reaction proceeds smoothly for a variety of alkyl and aryl picolines using a range of aryl sulfonyl chlorides. The reaction is believed to involve N-sulfonyl 4-alkylidene dihydropyridine intermediates and results in formal sulfonylation of unactivated picolyl C–H bonds. American Chemical Society 2023-02-27 /pmc/articles/PMC10028608/ /pubmed/36848377 http://dx.doi.org/10.1021/acs.joc.3c00017 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Tun, Soe L.
Shivers, Grant N.
Pigge, F. Christopher
C-Sulfonylation of 4-Alkylpyridines: Formal Picolyl C–H Activation via Alkylidene Dihydropyridine Intermediates
title C-Sulfonylation of 4-Alkylpyridines: Formal Picolyl C–H Activation via Alkylidene Dihydropyridine Intermediates
title_full C-Sulfonylation of 4-Alkylpyridines: Formal Picolyl C–H Activation via Alkylidene Dihydropyridine Intermediates
title_fullStr C-Sulfonylation of 4-Alkylpyridines: Formal Picolyl C–H Activation via Alkylidene Dihydropyridine Intermediates
title_full_unstemmed C-Sulfonylation of 4-Alkylpyridines: Formal Picolyl C–H Activation via Alkylidene Dihydropyridine Intermediates
title_short C-Sulfonylation of 4-Alkylpyridines: Formal Picolyl C–H Activation via Alkylidene Dihydropyridine Intermediates
title_sort c-sulfonylation of 4-alkylpyridines: formal picolyl c–h activation via alkylidene dihydropyridine intermediates
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10028608/
https://www.ncbi.nlm.nih.gov/pubmed/36848377
http://dx.doi.org/10.1021/acs.joc.3c00017
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AT piggefchristopher csulfonylationof4alkylpyridinesformalpicolylchactivationviaalkylidenedihydropyridineintermediates

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