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A Redox‐Active Nickel Complex that Acts as an Electron Mediator in Photochemical Giese Reactions
We report a simple protocol for the photochemical Giese addition of C(sp(3))‐centered radicals to a variety of electron‐poor olefins. The chemistry does not require external photoredox catalysts. Instead, it harnesses the excited‐state reactivity of 4‐alkyl‐1,4‐dihydropyridines (4‐alkyl‐DHPs) to gen...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6519288/ https://www.ncbi.nlm.nih.gov/pubmed/30747467 http://dx.doi.org/10.1002/anie.201814497 |
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author | van Leeuwen, Thomas Buzzetti, Luca Perego, Luca Alessandro Melchiorre, Paolo |
author_facet | van Leeuwen, Thomas Buzzetti, Luca Perego, Luca Alessandro Melchiorre, Paolo |
author_sort | van Leeuwen, Thomas |
collection | PubMed |
description | We report a simple protocol for the photochemical Giese addition of C(sp(3))‐centered radicals to a variety of electron‐poor olefins. The chemistry does not require external photoredox catalysts. Instead, it harnesses the excited‐state reactivity of 4‐alkyl‐1,4‐dihydropyridines (4‐alkyl‐DHPs) to generate alkyl radicals. Crucial for reactivity is the use of a catalytic amount of Ni(bpy)(3) (2+) (bpy=2,2′‐bipyridyl), which acts as an electron mediator to facilitate the redox processes involving fleeting and highly reactive intermediates. |
format | Online Article Text |
id | pubmed-6519288 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-65192882019-05-23 A Redox‐Active Nickel Complex that Acts as an Electron Mediator in Photochemical Giese Reactions van Leeuwen, Thomas Buzzetti, Luca Perego, Luca Alessandro Melchiorre, Paolo Angew Chem Int Ed Engl Communications We report a simple protocol for the photochemical Giese addition of C(sp(3))‐centered radicals to a variety of electron‐poor olefins. The chemistry does not require external photoredox catalysts. Instead, it harnesses the excited‐state reactivity of 4‐alkyl‐1,4‐dihydropyridines (4‐alkyl‐DHPs) to generate alkyl radicals. Crucial for reactivity is the use of a catalytic amount of Ni(bpy)(3) (2+) (bpy=2,2′‐bipyridyl), which acts as an electron mediator to facilitate the redox processes involving fleeting and highly reactive intermediates. John Wiley and Sons Inc. 2019-03-06 2019-04-01 /pmc/articles/PMC6519288/ /pubmed/30747467 http://dx.doi.org/10.1002/anie.201814497 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Communications van Leeuwen, Thomas Buzzetti, Luca Perego, Luca Alessandro Melchiorre, Paolo A Redox‐Active Nickel Complex that Acts as an Electron Mediator in Photochemical Giese Reactions |
title | A Redox‐Active Nickel Complex that Acts as an Electron Mediator in Photochemical Giese Reactions |
title_full | A Redox‐Active Nickel Complex that Acts as an Electron Mediator in Photochemical Giese Reactions |
title_fullStr | A Redox‐Active Nickel Complex that Acts as an Electron Mediator in Photochemical Giese Reactions |
title_full_unstemmed | A Redox‐Active Nickel Complex that Acts as an Electron Mediator in Photochemical Giese Reactions |
title_short | A Redox‐Active Nickel Complex that Acts as an Electron Mediator in Photochemical Giese Reactions |
title_sort | redox‐active nickel complex that acts as an electron mediator in photochemical giese reactions |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6519288/ https://www.ncbi.nlm.nih.gov/pubmed/30747467 http://dx.doi.org/10.1002/anie.201814497 |
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