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Water-promoted dehydrative coupling of 2-aminopyridines in heptane via a borrowing hydrogen strategy
A synthetic method for dehydrative N-benzylation promoted by water molecules in heptane using a π-benzylpalladium system has been developed. The presence of water significantly accelerates carbon–nitrogen bond formation, which is accomplished in an atom-economical process to afford the corresponding...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9034306/ https://www.ncbi.nlm.nih.gov/pubmed/35480450 http://dx.doi.org/10.1039/d1ra04118e |
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author | Nakayama, Taku Hikawa, Hidemasa Kikkawa, Shoko Azumaya, Isao |
author_facet | Nakayama, Taku Hikawa, Hidemasa Kikkawa, Shoko Azumaya, Isao |
author_sort | Nakayama, Taku |
collection | PubMed |
description | A synthetic method for dehydrative N-benzylation promoted by water molecules in heptane using a π-benzylpalladium system has been developed. The presence of water significantly accelerates carbon–nitrogen bond formation, which is accomplished in an atom-economical process to afford the corresponding N-monobenzylated products. A crossover experiment afforded H/D scrambled products, which is consistent with a borrowing hydrogen mechanism. Kinetic isotope effect measurements revealed that benzylic carbon–hydrogen bond cleavage was the rate-determining step. |
format | Online Article Text |
id | pubmed-9034306 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-90343062022-04-26 Water-promoted dehydrative coupling of 2-aminopyridines in heptane via a borrowing hydrogen strategy Nakayama, Taku Hikawa, Hidemasa Kikkawa, Shoko Azumaya, Isao RSC Adv Chemistry A synthetic method for dehydrative N-benzylation promoted by water molecules in heptane using a π-benzylpalladium system has been developed. The presence of water significantly accelerates carbon–nitrogen bond formation, which is accomplished in an atom-economical process to afford the corresponding N-monobenzylated products. A crossover experiment afforded H/D scrambled products, which is consistent with a borrowing hydrogen mechanism. Kinetic isotope effect measurements revealed that benzylic carbon–hydrogen bond cleavage was the rate-determining step. The Royal Society of Chemistry 2021-07-01 /pmc/articles/PMC9034306/ /pubmed/35480450 http://dx.doi.org/10.1039/d1ra04118e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Nakayama, Taku Hikawa, Hidemasa Kikkawa, Shoko Azumaya, Isao Water-promoted dehydrative coupling of 2-aminopyridines in heptane via a borrowing hydrogen strategy |
title | Water-promoted dehydrative coupling of 2-aminopyridines in heptane via a borrowing hydrogen strategy |
title_full | Water-promoted dehydrative coupling of 2-aminopyridines in heptane via a borrowing hydrogen strategy |
title_fullStr | Water-promoted dehydrative coupling of 2-aminopyridines in heptane via a borrowing hydrogen strategy |
title_full_unstemmed | Water-promoted dehydrative coupling of 2-aminopyridines in heptane via a borrowing hydrogen strategy |
title_short | Water-promoted dehydrative coupling of 2-aminopyridines in heptane via a borrowing hydrogen strategy |
title_sort | water-promoted dehydrative coupling of 2-aminopyridines in heptane via a borrowing hydrogen strategy |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9034306/ https://www.ncbi.nlm.nih.gov/pubmed/35480450 http://dx.doi.org/10.1039/d1ra04118e |
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