Transition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols

The base‐catalyzed allylic borylation of tertiary allylic alcohols allows the synthesis of 1,1‐disubstituted allyl boronates, in moderate to high yield. The unexpected tandem performance of the Lewis acid–base adduct, [Hbase](+)[MeO‐B(2)pin(2)](−) favored the formation of 1,2,3‐triborylated species...

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Autores principales: Miralles, Núria, Alam, Rauful, Szabó, Kálmán J., Fernández, Elena
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4804746/
https://www.ncbi.nlm.nih.gov/pubmed/26934578
http://dx.doi.org/10.1002/anie.201511255
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author Miralles, Núria
Alam, Rauful
Szabó, Kálmán J.
Fernández, Elena
author_facet Miralles, Núria
Alam, Rauful
Szabó, Kálmán J.
Fernández, Elena
author_sort Miralles, Núria
collection PubMed
description The base‐catalyzed allylic borylation of tertiary allylic alcohols allows the synthesis of 1,1‐disubstituted allyl boronates, in moderate to high yield. The unexpected tandem performance of the Lewis acid–base adduct, [Hbase](+)[MeO‐B(2)pin(2)](−) favored the formation of 1,2,3‐triborylated species from the tertiary allylic alcohols and 1‐propargylic cyclohexanol at 90 °C.
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spelling pubmed-48047462016-04-11 Transition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols Miralles, Núria Alam, Rauful Szabó, Kálmán J. Fernández, Elena Angew Chem Int Ed Engl Communications The base‐catalyzed allylic borylation of tertiary allylic alcohols allows the synthesis of 1,1‐disubstituted allyl boronates, in moderate to high yield. The unexpected tandem performance of the Lewis acid–base adduct, [Hbase](+)[MeO‐B(2)pin(2)](−) favored the formation of 1,2,3‐triborylated species from the tertiary allylic alcohols and 1‐propargylic cyclohexanol at 90 °C. John Wiley and Sons Inc. 2016-03-02 2016-03-18 /pmc/articles/PMC4804746/ /pubmed/26934578 http://dx.doi.org/10.1002/anie.201511255 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial (http://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Miralles, Núria
Alam, Rauful
Szabó, Kálmán J.
Fernández, Elena
Transition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols
title Transition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols
title_full Transition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols
title_fullStr Transition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols
title_full_unstemmed Transition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols
title_short Transition‐Metal‐Free Borylation of Allylic and Propargylic Alcohols
title_sort transition‐metal‐free borylation of allylic and propargylic alcohols
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4804746/
https://www.ncbi.nlm.nih.gov/pubmed/26934578
http://dx.doi.org/10.1002/anie.201511255
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