A Photocatalytic System Composed of Benzimidazolium Aryloxide and Tetramethylpiperidine 1-Oxyl to Promote Desulfonylative α-Oxyamination Reactions of α-Sulfonylketones

[Image: see text] A new photocatalytic system was developed for carrying out desulfonylative α-oxyamination reactions of α-sulfonylketones in which α-ketoalkyl radicals are generated. The catalytic system is composed of benzimidazolium aryloxide betaines (BI(+)–ArO(–)), serving as visible light-abso...

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Autores principales: Tanaka, Tsukasa, Kiuchi, Takehiro, Ooe, Yuuki, Iwamoto, Hajime, Takizawa, Shin-ya, Murata, Shigeru, Hasegawa, Eietsu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8829864/
https://www.ncbi.nlm.nih.gov/pubmed/35155957
http://dx.doi.org/10.1021/acsomega.1c06857
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author Tanaka, Tsukasa
Kiuchi, Takehiro
Ooe, Yuuki
Iwamoto, Hajime
Takizawa, Shin-ya
Murata, Shigeru
Hasegawa, Eietsu
author_facet Tanaka, Tsukasa
Kiuchi, Takehiro
Ooe, Yuuki
Iwamoto, Hajime
Takizawa, Shin-ya
Murata, Shigeru
Hasegawa, Eietsu
author_sort Tanaka, Tsukasa
collection PubMed
description [Image: see text] A new photocatalytic system was developed for carrying out desulfonylative α-oxyamination reactions of α-sulfonylketones in which α-ketoalkyl radicals are generated. The catalytic system is composed of benzimidazolium aryloxide betaines (BI(+)–ArO(–)), serving as visible light-absorbing electron donor photocatalysts, and 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO), playing dual roles as an electron donor for catalyst recycling and a reagent to capture the generated radical intermediates. Information about the detailed nature of BI(+)–ArO(–) and the photocatalytic processes with TEMPO was gained using absorption spectroscopy, electrochemical measurements, and density functional theory calculations.
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spelling pubmed-88298642022-02-11 A Photocatalytic System Composed of Benzimidazolium Aryloxide and Tetramethylpiperidine 1-Oxyl to Promote Desulfonylative α-Oxyamination Reactions of α-Sulfonylketones Tanaka, Tsukasa Kiuchi, Takehiro Ooe, Yuuki Iwamoto, Hajime Takizawa, Shin-ya Murata, Shigeru Hasegawa, Eietsu ACS Omega [Image: see text] A new photocatalytic system was developed for carrying out desulfonylative α-oxyamination reactions of α-sulfonylketones in which α-ketoalkyl radicals are generated. The catalytic system is composed of benzimidazolium aryloxide betaines (BI(+)–ArO(–)), serving as visible light-absorbing electron donor photocatalysts, and 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO), playing dual roles as an electron donor for catalyst recycling and a reagent to capture the generated radical intermediates. Information about the detailed nature of BI(+)–ArO(–) and the photocatalytic processes with TEMPO was gained using absorption spectroscopy, electrochemical measurements, and density functional theory calculations. American Chemical Society 2022-01-26 /pmc/articles/PMC8829864/ /pubmed/35155957 http://dx.doi.org/10.1021/acsomega.1c06857 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Tanaka, Tsukasa
Kiuchi, Takehiro
Ooe, Yuuki
Iwamoto, Hajime
Takizawa, Shin-ya
Murata, Shigeru
Hasegawa, Eietsu
A Photocatalytic System Composed of Benzimidazolium Aryloxide and Tetramethylpiperidine 1-Oxyl to Promote Desulfonylative α-Oxyamination Reactions of α-Sulfonylketones
title A Photocatalytic System Composed of Benzimidazolium Aryloxide and Tetramethylpiperidine 1-Oxyl to Promote Desulfonylative α-Oxyamination Reactions of α-Sulfonylketones
title_full A Photocatalytic System Composed of Benzimidazolium Aryloxide and Tetramethylpiperidine 1-Oxyl to Promote Desulfonylative α-Oxyamination Reactions of α-Sulfonylketones
title_fullStr A Photocatalytic System Composed of Benzimidazolium Aryloxide and Tetramethylpiperidine 1-Oxyl to Promote Desulfonylative α-Oxyamination Reactions of α-Sulfonylketones
title_full_unstemmed A Photocatalytic System Composed of Benzimidazolium Aryloxide and Tetramethylpiperidine 1-Oxyl to Promote Desulfonylative α-Oxyamination Reactions of α-Sulfonylketones
title_short A Photocatalytic System Composed of Benzimidazolium Aryloxide and Tetramethylpiperidine 1-Oxyl to Promote Desulfonylative α-Oxyamination Reactions of α-Sulfonylketones
title_sort photocatalytic system composed of benzimidazolium aryloxide and tetramethylpiperidine 1-oxyl to promote desulfonylative α-oxyamination reactions of α-sulfonylketones
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8829864/
https://www.ncbi.nlm.nih.gov/pubmed/35155957
http://dx.doi.org/10.1021/acsomega.1c06857
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