Rh(ii)-catalyzed branch-selective C–H alkylation of aryl sulfonamides with vinylsilanes

Rhodium(ii)-catalyzed unusual branch-selective ortho-C–H alkylation of aryl sulfonamides with vinylsilanes was achieved using an 8-aminoquinoline directing group. Notably, the para-substituted aryl sulfonamides gave mono-(branched)alkylated products exclusively without the formation of any double C–...

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Detalles Bibliográficos
Autores principales: Rej, Supriya, Chatani, Naoto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7069504/
https://www.ncbi.nlm.nih.gov/pubmed/32206270
http://dx.doi.org/10.1039/c9sc04308j
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author Rej, Supriya
Chatani, Naoto
author_facet Rej, Supriya
Chatani, Naoto
author_sort Rej, Supriya
collection PubMed
description Rhodium(ii)-catalyzed unusual branch-selective ortho-C–H alkylation of aryl sulfonamides with vinylsilanes was achieved using an 8-aminoquinoline directing group. Notably, the para-substituted aryl sulfonamides gave mono-(branched)alkylated products exclusively without the formation of any double C–H alkylated byproducts. The results of deuterium labeling experiments suggest that both hydrometalation and carbometalation pathways are involved in this conversion.
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spelling pubmed-70695042020-03-23 Rh(ii)-catalyzed branch-selective C–H alkylation of aryl sulfonamides with vinylsilanes Rej, Supriya Chatani, Naoto Chem Sci Chemistry Rhodium(ii)-catalyzed unusual branch-selective ortho-C–H alkylation of aryl sulfonamides with vinylsilanes was achieved using an 8-aminoquinoline directing group. Notably, the para-substituted aryl sulfonamides gave mono-(branched)alkylated products exclusively without the formation of any double C–H alkylated byproducts. The results of deuterium labeling experiments suggest that both hydrometalation and carbometalation pathways are involved in this conversion. Royal Society of Chemistry 2019-11-11 /pmc/articles/PMC7069504/ /pubmed/32206270 http://dx.doi.org/10.1039/c9sc04308j Text en This journal is © The Royal Society of Chemistry 2020 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Rej, Supriya
Chatani, Naoto
Rh(ii)-catalyzed branch-selective C–H alkylation of aryl sulfonamides with vinylsilanes
title Rh(ii)-catalyzed branch-selective C–H alkylation of aryl sulfonamides with vinylsilanes
title_full Rh(ii)-catalyzed branch-selective C–H alkylation of aryl sulfonamides with vinylsilanes
title_fullStr Rh(ii)-catalyzed branch-selective C–H alkylation of aryl sulfonamides with vinylsilanes
title_full_unstemmed Rh(ii)-catalyzed branch-selective C–H alkylation of aryl sulfonamides with vinylsilanes
title_short Rh(ii)-catalyzed branch-selective C–H alkylation of aryl sulfonamides with vinylsilanes
title_sort rh(ii)-catalyzed branch-selective c–h alkylation of aryl sulfonamides with vinylsilanes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7069504/
https://www.ncbi.nlm.nih.gov/pubmed/32206270
http://dx.doi.org/10.1039/c9sc04308j
work_keys_str_mv AT rejsupriya rhiicatalyzedbranchselectivechalkylationofarylsulfonamideswithvinylsilanes
AT chataninaoto rhiicatalyzedbranchselectivechalkylationofarylsulfonamideswithvinylsilanes

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