Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions

The formation and use of iminyl radicals in novel and divergent hydroimination and iminohydroxylation cyclization reactions has been accomplished through the design of a new class of reactive O-aryl oximes. Owing to their low reduction potentials, the inexpensive organic dye eosin Y could be used as...

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Detalles Bibliográficos
Autores principales: Davies, Jacob, Booth, Samuel G, Essafi, Stephanie, Dryfe, Robert A W, Leonori, Daniele
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2015
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4648045/
https://www.ncbi.nlm.nih.gov/pubmed/26412046
http://dx.doi.org/10.1002/anie.201507641
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author Davies, Jacob
Booth, Samuel G
Essafi, Stephanie
Dryfe, Robert A W
Leonori, Daniele
author_facet Davies, Jacob
Booth, Samuel G
Essafi, Stephanie
Dryfe, Robert A W
Leonori, Daniele
author_sort Davies, Jacob
collection PubMed
description The formation and use of iminyl radicals in novel and divergent hydroimination and iminohydroxylation cyclization reactions has been accomplished through the design of a new class of reactive O-aryl oximes. Owing to their low reduction potentials, the inexpensive organic dye eosin Y could be used as the photocatalyst of the organocatalytic hydroimination reaction. Furthermore, reaction conditions for a unique iminohydroxylation were identified; visible-light-mediated electron transfer from novel electron donor–acceptor complexes of the oximes and Et(3)N was proposed as a key step of this process.
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spelling pubmed-46480452015-11-24 Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions Davies, Jacob Booth, Samuel G Essafi, Stephanie Dryfe, Robert A W Leonori, Daniele Angew Chem Int Ed Engl Communications The formation and use of iminyl radicals in novel and divergent hydroimination and iminohydroxylation cyclization reactions has been accomplished through the design of a new class of reactive O-aryl oximes. Owing to their low reduction potentials, the inexpensive organic dye eosin Y could be used as the photocatalyst of the organocatalytic hydroimination reaction. Furthermore, reaction conditions for a unique iminohydroxylation were identified; visible-light-mediated electron transfer from novel electron donor–acceptor complexes of the oximes and Et(3)N was proposed as a key step of this process. WILEY-VCH Verlag 2015-11-16 2015-09-28 /pmc/articles/PMC4648045/ /pubmed/26412046 http://dx.doi.org/10.1002/anie.201507641 Text en © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. https://creativecommons.org/licenses/by/4.0/ © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Davies, Jacob
Booth, Samuel G
Essafi, Stephanie
Dryfe, Robert A W
Leonori, Daniele
Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions
title Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions
title_full Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions
title_fullStr Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions
title_full_unstemmed Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions
title_short Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions
title_sort visible-light-mediated generation of nitrogen-centered radicals: metal-free hydroimination and iminohydroxylation cyclization reactions
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4648045/
https://www.ncbi.nlm.nih.gov/pubmed/26412046
http://dx.doi.org/10.1002/anie.201507641
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