Cargando…

Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters

The synthesis of alkyl boronic esters by direct decarboxylative radical addition of carboxylic acids to vinyl boronic esters is described. The reaction proceeds under mild photoredox catalysis and involves an unprecedented single‐electron reduction of an α‐boryl radical intermediate to the correspon...

Descripción completa

Detalles Bibliográficos
Autores principales: Noble, Adam, Mega, Riccardo S., Pflästerer, Daniel, Myers, Eddie L., Aggarwal, Varinder K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5838549/
https://www.ncbi.nlm.nih.gov/pubmed/29316095
http://dx.doi.org/10.1002/anie.201712186
_version_ 1783304282919927808
author Noble, Adam
Mega, Riccardo S.
Pflästerer, Daniel
Myers, Eddie L.
Aggarwal, Varinder K.
author_facet Noble, Adam
Mega, Riccardo S.
Pflästerer, Daniel
Myers, Eddie L.
Aggarwal, Varinder K.
author_sort Noble, Adam
collection PubMed
description The synthesis of alkyl boronic esters by direct decarboxylative radical addition of carboxylic acids to vinyl boronic esters is described. The reaction proceeds under mild photoredox catalysis and involves an unprecedented single‐electron reduction of an α‐boryl radical intermediate to the corresponding anion. The reaction is amenable to a diverse range of substrates, including α‐amino, α‐oxy, and alkyl carboxylic acids, thus providing a novel method to rapidly access boron‐containing molecules of potential biological importance.
format Online
Article
Text
id pubmed-5838549
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher John Wiley and Sons Inc.
record_format MEDLINE/PubMed
spelling pubmed-58385492018-03-12 Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters Noble, Adam Mega, Riccardo S. Pflästerer, Daniel Myers, Eddie L. Aggarwal, Varinder K. Angew Chem Int Ed Engl Communications The synthesis of alkyl boronic esters by direct decarboxylative radical addition of carboxylic acids to vinyl boronic esters is described. The reaction proceeds under mild photoredox catalysis and involves an unprecedented single‐electron reduction of an α‐boryl radical intermediate to the corresponding anion. The reaction is amenable to a diverse range of substrates, including α‐amino, α‐oxy, and alkyl carboxylic acids, thus providing a novel method to rapidly access boron‐containing molecules of potential biological importance. John Wiley and Sons Inc. 2018-01-26 2018-02-19 /pmc/articles/PMC5838549/ /pubmed/29316095 http://dx.doi.org/10.1002/anie.201712186 Text en © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://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
Noble, Adam
Mega, Riccardo S.
Pflästerer, Daniel
Myers, Eddie L.
Aggarwal, Varinder K.
Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters
title Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters
title_full Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters
title_fullStr Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters
title_full_unstemmed Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters
title_short Visible‐Light‐Mediated Decarboxylative Radical Additions to Vinyl Boronic Esters: Rapid Access to γ‐Amino Boronic Esters
title_sort visible‐light‐mediated decarboxylative radical additions to vinyl boronic esters: rapid access to γ‐amino boronic esters
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5838549/
https://www.ncbi.nlm.nih.gov/pubmed/29316095
http://dx.doi.org/10.1002/anie.201712186
work_keys_str_mv AT nobleadam visiblelightmediateddecarboxylativeradicaladditionstovinylboronicestersrapidaccesstogaminoboronicesters
AT megariccardos visiblelightmediateddecarboxylativeradicaladditionstovinylboronicestersrapidaccesstogaminoboronicesters
AT pflastererdaniel visiblelightmediateddecarboxylativeradicaladditionstovinylboronicestersrapidaccesstogaminoboronicesters
AT myerseddiel visiblelightmediateddecarboxylativeradicaladditionstovinylboronicestersrapidaccesstogaminoboronicesters
AT aggarwalvarinderk visiblelightmediateddecarboxylativeradicaladditionstovinylboronicestersrapidaccesstogaminoboronicesters