Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp(2))–C(sp(3)) Cross‐Couplings in Flow

We report herein a new method for the photoredox activation of boronic esters. Using these reagents, an efficient and high‐throughput continuous flow process was developed to perform a dual iridium‐ and nickel‐catalyzed C(sp(2))–C(sp(3)) coupling by circumventing solubility issues associated with po...

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Autores principales: Lima, Fabio, Kabeshov, Mikhail A., Tran, Duc N., Battilocchio, Claudio, Sedelmeier, Joerg, Sedelmeier, Gottfried, Schenkel, Berthold, Ley, Steven V.
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/PMC5113707/
https://www.ncbi.nlm.nih.gov/pubmed/27709749
http://dx.doi.org/10.1002/anie.201605548
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author Lima, Fabio
Kabeshov, Mikhail A.
Tran, Duc N.
Battilocchio, Claudio
Sedelmeier, Joerg
Sedelmeier, Gottfried
Schenkel, Berthold
Ley, Steven V.
author_facet Lima, Fabio
Kabeshov, Mikhail A.
Tran, Duc N.
Battilocchio, Claudio
Sedelmeier, Joerg
Sedelmeier, Gottfried
Schenkel, Berthold
Ley, Steven V.
author_sort Lima, Fabio
collection PubMed
description We report herein a new method for the photoredox activation of boronic esters. Using these reagents, an efficient and high‐throughput continuous flow process was developed to perform a dual iridium‐ and nickel‐catalyzed C(sp(2))–C(sp(3)) coupling by circumventing solubility issues associated with potassium trifluoroborate salts. Formation of an adduct with a pyridine‐derived Lewis base was found to be essential for the photoredox activation of the boronic esters. Based on these results we were able to develop a further simplified visible light mediated C(sp(2))–C(sp(3)) coupling method using boronic esters and cyano heteroarenes under flow conditions.
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spelling pubmed-51137072016-11-30 Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp(2))–C(sp(3)) Cross‐Couplings in Flow Lima, Fabio Kabeshov, Mikhail A. Tran, Duc N. Battilocchio, Claudio Sedelmeier, Joerg Sedelmeier, Gottfried Schenkel, Berthold Ley, Steven V. Angew Chem Int Ed Engl Communications We report herein a new method for the photoredox activation of boronic esters. Using these reagents, an efficient and high‐throughput continuous flow process was developed to perform a dual iridium‐ and nickel‐catalyzed C(sp(2))–C(sp(3)) coupling by circumventing solubility issues associated with potassium trifluoroborate salts. Formation of an adduct with a pyridine‐derived Lewis base was found to be essential for the photoredox activation of the boronic esters. Based on these results we were able to develop a further simplified visible light mediated C(sp(2))–C(sp(3)) coupling method using boronic esters and cyano heteroarenes under flow conditions. John Wiley and Sons Inc. 2016-10-06 2016-11-02 /pmc/articles/PMC5113707/ /pubmed/27709749 http://dx.doi.org/10.1002/anie.201605548 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 (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
Lima, Fabio
Kabeshov, Mikhail A.
Tran, Duc N.
Battilocchio, Claudio
Sedelmeier, Joerg
Sedelmeier, Gottfried
Schenkel, Berthold
Ley, Steven V.
Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp(2))–C(sp(3)) Cross‐Couplings in Flow
title Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp(2))–C(sp(3)) Cross‐Couplings in Flow
title_full Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp(2))–C(sp(3)) Cross‐Couplings in Flow
title_fullStr Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp(2))–C(sp(3)) Cross‐Couplings in Flow
title_full_unstemmed Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp(2))–C(sp(3)) Cross‐Couplings in Flow
title_short Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp(2))–C(sp(3)) Cross‐Couplings in Flow
title_sort visible light activation of boronic esters enables efficient photoredox c(sp(2))–c(sp(3)) cross‐couplings in flow
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5113707/
https://www.ncbi.nlm.nih.gov/pubmed/27709749
http://dx.doi.org/10.1002/anie.201605548
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