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Arylboration of Enecarbamates for the Synthesis of Borylated Saturated N‐Heterocycles
Two catalytic systems have been developed for the arylboration of endocyclic enecarbamates to deliver synthetically versatile borylated saturated N‐heterocycles in good regio‐ and diastereoselectivities. A Cu/Pd dual catalytic reaction enables the synthesis of borylated, α‐arylated azetidines, while...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9643676/ https://www.ncbi.nlm.nih.gov/pubmed/36250954 http://dx.doi.org/10.1002/anie.202212117 |
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author | Trammel, Grace L. Kannangara, Prashansa B. Vasko, Dmytro Datsenko, Oleksandr Mykhailiuk, Pavel Brown, M. Kevin |
author_facet | Trammel, Grace L. Kannangara, Prashansa B. Vasko, Dmytro Datsenko, Oleksandr Mykhailiuk, Pavel Brown, M. Kevin |
author_sort | Trammel, Grace L. |
collection | PubMed |
description | Two catalytic systems have been developed for the arylboration of endocyclic enecarbamates to deliver synthetically versatile borylated saturated N‐heterocycles in good regio‐ and diastereoselectivities. A Cu/Pd dual catalytic reaction enables the synthesis of borylated, α‐arylated azetidines, while a Ni‐catalysed arylboration reaction efficiently functionalizes 5‐, 6‐, and 7‐membered enecarbamates. In the case of the Cu/Pd‐system, a remarkable additive effect was identified that allowed for broader scope. The products are synthetically useful, as demonstrated by manipulations of the boronic ester to access biologically active compounds. |
format | Online Article Text |
id | pubmed-9643676 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-96436762023-01-10 Arylboration of Enecarbamates for the Synthesis of Borylated Saturated N‐Heterocycles Trammel, Grace L. Kannangara, Prashansa B. Vasko, Dmytro Datsenko, Oleksandr Mykhailiuk, Pavel Brown, M. Kevin Angew Chem Int Ed Engl Communications Two catalytic systems have been developed for the arylboration of endocyclic enecarbamates to deliver synthetically versatile borylated saturated N‐heterocycles in good regio‐ and diastereoselectivities. A Cu/Pd dual catalytic reaction enables the synthesis of borylated, α‐arylated azetidines, while a Ni‐catalysed arylboration reaction efficiently functionalizes 5‐, 6‐, and 7‐membered enecarbamates. In the case of the Cu/Pd‐system, a remarkable additive effect was identified that allowed for broader scope. The products are synthetically useful, as demonstrated by manipulations of the boronic ester to access biologically active compounds. John Wiley and Sons Inc. 2022-10-17 2022-11-14 /pmc/articles/PMC9643676/ /pubmed/36250954 http://dx.doi.org/10.1002/anie.202212117 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Trammel, Grace L. Kannangara, Prashansa B. Vasko, Dmytro Datsenko, Oleksandr Mykhailiuk, Pavel Brown, M. Kevin Arylboration of Enecarbamates for the Synthesis of Borylated Saturated N‐Heterocycles |
title | Arylboration of Enecarbamates for the Synthesis of Borylated Saturated N‐Heterocycles |
title_full | Arylboration of Enecarbamates for the Synthesis of Borylated Saturated N‐Heterocycles |
title_fullStr | Arylboration of Enecarbamates for the Synthesis of Borylated Saturated N‐Heterocycles |
title_full_unstemmed | Arylboration of Enecarbamates for the Synthesis of Borylated Saturated N‐Heterocycles |
title_short | Arylboration of Enecarbamates for the Synthesis of Borylated Saturated N‐Heterocycles |
title_sort | arylboration of enecarbamates for the synthesis of borylated saturated n‐heterocycles |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9643676/ https://www.ncbi.nlm.nih.gov/pubmed/36250954 http://dx.doi.org/10.1002/anie.202212117 |
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