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Rhodium-catalyzed regioselective addition of the ortho C–H bond in aromatic amides to the C–C double bond in α,β-unsaturated γ-lactones and dihydrofurans
An unprecedented C–H alkylation using α,β-unsaturated γ-lactones (butenolides) and dihydrofurans was achieved by the Rh-catalyzed reaction of benzamides. C–C bond formation occurs between the ortho-position of the benzamide derivative and the γ-position of the butenolide or the α-position of the dih...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Royal Society of Chemistry
2016
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5952307/ https://www.ncbi.nlm.nih.gov/pubmed/29861979 http://dx.doi.org/10.1039/c5sc03110a |
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author | Shibata, Kaname Chatani, Naoto |
author_facet | Shibata, Kaname Chatani, Naoto |
author_sort | Shibata, Kaname |
collection | PubMed |
description | An unprecedented C–H alkylation using α,β-unsaturated γ-lactones (butenolides) and dihydrofurans was achieved by the Rh-catalyzed reaction of benzamides. C–C bond formation occurs between the ortho-position of the benzamide derivative and the γ-position of the butenolide or the α-position of the dihydrofuran. The presence of an 8-aminoquinoline directing group is crucial for the success of the reaction. The results of deuterium labeling experiments indicate that the cleavage of the C–H bond is reversible and suggest that a migratory carbene insertion is involved as the key step. |
format | Online Article Text |
id | pubmed-5952307 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-59523072018-06-01 Rhodium-catalyzed regioselective addition of the ortho C–H bond in aromatic amides to the C–C double bond in α,β-unsaturated γ-lactones and dihydrofurans Shibata, Kaname Chatani, Naoto Chem Sci Chemistry An unprecedented C–H alkylation using α,β-unsaturated γ-lactones (butenolides) and dihydrofurans was achieved by the Rh-catalyzed reaction of benzamides. C–C bond formation occurs between the ortho-position of the benzamide derivative and the γ-position of the butenolide or the α-position of the dihydrofuran. The presence of an 8-aminoquinoline directing group is crucial for the success of the reaction. The results of deuterium labeling experiments indicate that the cleavage of the C–H bond is reversible and suggest that a migratory carbene insertion is involved as the key step. Royal Society of Chemistry 2016-01-01 2015-09-25 /pmc/articles/PMC5952307/ /pubmed/29861979 http://dx.doi.org/10.1039/c5sc03110a Text en This journal is © The Royal Society of Chemistry 2016 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 Shibata, Kaname Chatani, Naoto Rhodium-catalyzed regioselective addition of the ortho C–H bond in aromatic amides to the C–C double bond in α,β-unsaturated γ-lactones and dihydrofurans |
title | Rhodium-catalyzed regioselective addition of the ortho C–H bond in aromatic amides to the C–C double bond in α,β-unsaturated γ-lactones and dihydrofurans
|
title_full | Rhodium-catalyzed regioselective addition of the ortho C–H bond in aromatic amides to the C–C double bond in α,β-unsaturated γ-lactones and dihydrofurans
|
title_fullStr | Rhodium-catalyzed regioselective addition of the ortho C–H bond in aromatic amides to the C–C double bond in α,β-unsaturated γ-lactones and dihydrofurans
|
title_full_unstemmed | Rhodium-catalyzed regioselective addition of the ortho C–H bond in aromatic amides to the C–C double bond in α,β-unsaturated γ-lactones and dihydrofurans
|
title_short | Rhodium-catalyzed regioselective addition of the ortho C–H bond in aromatic amides to the C–C double bond in α,β-unsaturated γ-lactones and dihydrofurans
|
title_sort | rhodium-catalyzed regioselective addition of the ortho c–h bond in aromatic amides to the c–c double bond in α,β-unsaturated γ-lactones and dihydrofurans |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5952307/ https://www.ncbi.nlm.nih.gov/pubmed/29861979 http://dx.doi.org/10.1039/c5sc03110a |
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