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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...

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Autores principales: Trammel, Grace L., Kannangara, Prashansa B., Vasko, Dmytro, Datsenko, Oleksandr, Mykhailiuk, Pavel, Brown, M. Kevin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
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.
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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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