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Selective C(sp(3))–H arylation/alkylation of alkanes enabled by paired electrocatalysis

We report a combination of electrocatalysis and photoredox catalysis to perform selective C(sp(3))–H arylation/alkylation of alkanes, in which a binary catalytic system based on earth-abundant iron and nickel is applied. Reaction selectivity between two-component C(sp(3))–H arylation and three-compo...

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Autores principales: Zou, Long, Xiang, Siqi, Sun, Rui, Lu, Qingquan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10693613/
https://www.ncbi.nlm.nih.gov/pubmed/38042911
http://dx.doi.org/10.1038/s41467-023-43791-1
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author Zou, Long
Xiang, Siqi
Sun, Rui
Lu, Qingquan
author_facet Zou, Long
Xiang, Siqi
Sun, Rui
Lu, Qingquan
author_sort Zou, Long
collection PubMed
description We report a combination of electrocatalysis and photoredox catalysis to perform selective C(sp(3))–H arylation/alkylation of alkanes, in which a binary catalytic system based on earth-abundant iron and nickel is applied. Reaction selectivity between two-component C(sp(3))–H arylation and three-component C(sp(3))–H alkylation is tuned by modulating the applied current and light source. Importantly, an ultra-low anodic potential (~0.23 V vs. Ag/AgCl) is applied in this protocol, thus enabling compatibility with a variety of functional groups (>70 examples). The robustness of the method is further demonstrated on a preparative scale and applied to late-stage diversification of natural products and pharmaceutical derivatives.
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spelling pubmed-106936132023-12-04 Selective C(sp(3))–H arylation/alkylation of alkanes enabled by paired electrocatalysis Zou, Long Xiang, Siqi Sun, Rui Lu, Qingquan Nat Commun Article We report a combination of electrocatalysis and photoredox catalysis to perform selective C(sp(3))–H arylation/alkylation of alkanes, in which a binary catalytic system based on earth-abundant iron and nickel is applied. Reaction selectivity between two-component C(sp(3))–H arylation and three-component C(sp(3))–H alkylation is tuned by modulating the applied current and light source. Importantly, an ultra-low anodic potential (~0.23 V vs. Ag/AgCl) is applied in this protocol, thus enabling compatibility with a variety of functional groups (>70 examples). The robustness of the method is further demonstrated on a preparative scale and applied to late-stage diversification of natural products and pharmaceutical derivatives. Nature Publishing Group UK 2023-12-02 /pmc/articles/PMC10693613/ /pubmed/38042911 http://dx.doi.org/10.1038/s41467-023-43791-1 Text en © The Author(s) 2023 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Zou, Long
Xiang, Siqi
Sun, Rui
Lu, Qingquan
Selective C(sp(3))–H arylation/alkylation of alkanes enabled by paired electrocatalysis
title Selective C(sp(3))–H arylation/alkylation of alkanes enabled by paired electrocatalysis
title_full Selective C(sp(3))–H arylation/alkylation of alkanes enabled by paired electrocatalysis
title_fullStr Selective C(sp(3))–H arylation/alkylation of alkanes enabled by paired electrocatalysis
title_full_unstemmed Selective C(sp(3))–H arylation/alkylation of alkanes enabled by paired electrocatalysis
title_short Selective C(sp(3))–H arylation/alkylation of alkanes enabled by paired electrocatalysis
title_sort selective c(sp(3))–h arylation/alkylation of alkanes enabled by paired electrocatalysis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10693613/
https://www.ncbi.nlm.nih.gov/pubmed/38042911
http://dx.doi.org/10.1038/s41467-023-43791-1
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