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Formal β‐C−H Arylation of Aldehydes and Ketones by Cooperative Nickel and Photoredox Catalysis
α‐C−H‐functionalization of ketones and aldehydes has been intensively explored in organic synthesis. The functionalization of unactivated β‐C−H bonds in such carbonyl compounds is less well investigated and developing a general method for their β‐C−H arylation remains challenging. Herein we report a...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9400853/ https://www.ncbi.nlm.nih.gov/pubmed/35656716 http://dx.doi.org/10.1002/anie.202206533 |
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author | Liu, Kun Studer, Armido |
author_facet | Liu, Kun Studer, Armido |
author_sort | Liu, Kun |
collection | PubMed |
description | α‐C−H‐functionalization of ketones and aldehydes has been intensively explored in organic synthesis. The functionalization of unactivated β‐C−H bonds in such carbonyl compounds is less well investigated and developing a general method for their β‐C−H arylation remains challenging. Herein we report a method that uses cooperative nickel and photoredox catalysis for the formal β‐C−H arylation of aldehydes and ketones with (hetero)aryl bromides. The method features mild conditions, remarkable scope and wide functional group tolerance. Importantly, the introduced synthetic strategy also allows the β‐alkenylation, β‐alkynylation and β‐acylation of aldehydes under similar conditions. Mechanistic studies revealed that this transformation proceeds through a single electron oxidation/Ni‐mediated coupling/reductive elimination cascade. |
format | Online Article Text |
id | pubmed-9400853 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-94008532022-08-26 Formal β‐C−H Arylation of Aldehydes and Ketones by Cooperative Nickel and Photoredox Catalysis Liu, Kun Studer, Armido Angew Chem Int Ed Engl Communications α‐C−H‐functionalization of ketones and aldehydes has been intensively explored in organic synthesis. The functionalization of unactivated β‐C−H bonds in such carbonyl compounds is less well investigated and developing a general method for their β‐C−H arylation remains challenging. Herein we report a method that uses cooperative nickel and photoredox catalysis for the formal β‐C−H arylation of aldehydes and ketones with (hetero)aryl bromides. The method features mild conditions, remarkable scope and wide functional group tolerance. Importantly, the introduced synthetic strategy also allows the β‐alkenylation, β‐alkynylation and β‐acylation of aldehydes under similar conditions. Mechanistic studies revealed that this transformation proceeds through a single electron oxidation/Ni‐mediated coupling/reductive elimination cascade. John Wiley and Sons Inc. 2022-06-23 2022-08-01 /pmc/articles/PMC9400853/ /pubmed/35656716 http://dx.doi.org/10.1002/anie.202206533 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ (https://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 Liu, Kun Studer, Armido Formal β‐C−H Arylation of Aldehydes and Ketones by Cooperative Nickel and Photoredox Catalysis |
title | Formal β‐C−H Arylation of Aldehydes and Ketones by Cooperative Nickel and Photoredox Catalysis |
title_full | Formal β‐C−H Arylation of Aldehydes and Ketones by Cooperative Nickel and Photoredox Catalysis |
title_fullStr | Formal β‐C−H Arylation of Aldehydes and Ketones by Cooperative Nickel and Photoredox Catalysis |
title_full_unstemmed | Formal β‐C−H Arylation of Aldehydes and Ketones by Cooperative Nickel and Photoredox Catalysis |
title_short | Formal β‐C−H Arylation of Aldehydes and Ketones by Cooperative Nickel and Photoredox Catalysis |
title_sort | formal β‐c−h arylation of aldehydes and ketones by cooperative nickel and photoredox catalysis |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9400853/ https://www.ncbi.nlm.nih.gov/pubmed/35656716 http://dx.doi.org/10.1002/anie.202206533 |
work_keys_str_mv | AT liukun formalbcharylationofaldehydesandketonesbycooperativenickelandphotoredoxcatalysis AT studerarmido formalbcharylationofaldehydesandketonesbycooperativenickelandphotoredoxcatalysis |