Electron and hydrogen atom donor photocatalysts in situ generated from benzimidazolium salts and hydride reagents
Photocatalytic systems consisting of 2-substituted benzimidazoliums (BI+–R, R = polycyclic aryl, triarylamine or phenyl-sulfate) and stoichiometric hydride donor reagents were developed. Light emitting diode irradiation of these photocatalysts in the presence of NaBH4 or picoline borane promotes des...
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| Format: | Article |
| Language: | English |
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Elsevier
2023-08-01
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| Series: | Journal of Photochemistry and Photobiology |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666469023000362 |
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| author | Ryo Miyajima Takehiro Kiuchi Yuki Ooe Hajime Iwamoto Shin-ya Takizawa Eietsu Hasegawa |
| author_facet | Ryo Miyajima Takehiro Kiuchi Yuki Ooe Hajime Iwamoto Shin-ya Takizawa Eietsu Hasegawa |
| author_sort | Ryo Miyajima |
| collection | DOAJ |
| description | Photocatalytic systems consisting of 2-substituted benzimidazoliums (BI+–R, R = polycyclic aryl, triarylamine or phenyl-sulfate) and stoichiometric hydride donor reagents were developed. Light emitting diode irradiation of these photocatalysts in the presence of NaBH4 or picoline borane promotes desulfonylation reactions of an N-sulfonyl indole, N-sulfonyl amide and α-sulfonyl ketone. Absorption spectroscopic and redox potential measurements as well as density functional theory calculations were carried out to gain mechanistic information. Benzimidazolines (BIH–R), generated in situ by hydride reduction of BI+–R, serve as both an electron and hydrogen atom donor photocatalysts in these reductive desulfonylation reactions, which contrasts to ordinary reducing photocatalysts that simply donate electrons. |
| first_indexed | 2024-03-12T19:32:36Z |
| format | Article |
| id | doaj.art-7d8942de3a9d4b0984f3e632b0b4dbf6 |
| institution | Directory Open Access Journal |
| issn | 2666-4690 |
| language | English |
| last_indexed | 2024-03-12T19:32:36Z |
| publishDate | 2023-08-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Photochemistry and Photobiology |
| spelling | doaj.art-7d8942de3a9d4b0984f3e632b0b4dbf62023-08-02T04:25:05ZengElsevierJournal of Photochemistry and Photobiology2666-46902023-08-0116100195Electron and hydrogen atom donor photocatalysts in situ generated from benzimidazolium salts and hydride reagentsRyo Miyajima0Takehiro Kiuchi1Yuki Ooe2Hajime Iwamoto3Shin-ya Takizawa4Eietsu Hasegawa5Department of Chemistry, Faculty of Science, Niigata University, 8050 Ikarashi-2, Nishi-ku, Niigata, 950-2181, JapanDepartment of Chemistry, Faculty of Science, Niigata University, 8050 Ikarashi-2, Nishi-ku, Niigata, 950-2181, JapanDepartment of Chemistry, Faculty of Science, Niigata University, 8050 Ikarashi-2, Nishi-ku, Niigata, 950-2181, JapanDepartment of Chemistry, Faculty of Science, Niigata University, 8050 Ikarashi-2, Nishi-ku, Niigata, 950-2181, JapanDepartment of Basic Science, Graduate School of Arts and Sciences, The University of Tokyo, 3-8-1 Komaba, Meguro-ku, Tokyo, 153-8902, JapanDepartment of Chemistry, Faculty of Science, Niigata University, 8050 Ikarashi-2, Nishi-ku, Niigata, 950-2181, Japan; Corresponding author.Photocatalytic systems consisting of 2-substituted benzimidazoliums (BI+–R, R = polycyclic aryl, triarylamine or phenyl-sulfate) and stoichiometric hydride donor reagents were developed. Light emitting diode irradiation of these photocatalysts in the presence of NaBH4 or picoline borane promotes desulfonylation reactions of an N-sulfonyl indole, N-sulfonyl amide and α-sulfonyl ketone. Absorption spectroscopic and redox potential measurements as well as density functional theory calculations were carried out to gain mechanistic information. Benzimidazolines (BIH–R), generated in situ by hydride reduction of BI+–R, serve as both an electron and hydrogen atom donor photocatalysts in these reductive desulfonylation reactions, which contrasts to ordinary reducing photocatalysts that simply donate electrons.http://www.sciencedirect.com/science/article/pii/S2666469023000362Benzimidazoline and benzimidazolium coupleHydride donor reagentElectron and hydrogen atom donorReducing photocatalystReductive desulfonylation |
| spellingShingle | Ryo Miyajima Takehiro Kiuchi Yuki Ooe Hajime Iwamoto Shin-ya Takizawa Eietsu Hasegawa Electron and hydrogen atom donor photocatalysts in situ generated from benzimidazolium salts and hydride reagents Journal of Photochemistry and Photobiology Benzimidazoline and benzimidazolium couple Hydride donor reagent Electron and hydrogen atom donor Reducing photocatalyst Reductive desulfonylation |
| title | Electron and hydrogen atom donor photocatalysts in situ generated from benzimidazolium salts and hydride reagents |
| title_full | Electron and hydrogen atom donor photocatalysts in situ generated from benzimidazolium salts and hydride reagents |
| title_fullStr | Electron and hydrogen atom donor photocatalysts in situ generated from benzimidazolium salts and hydride reagents |
| title_full_unstemmed | Electron and hydrogen atom donor photocatalysts in situ generated from benzimidazolium salts and hydride reagents |
| title_short | Electron and hydrogen atom donor photocatalysts in situ generated from benzimidazolium salts and hydride reagents |
| title_sort | electron and hydrogen atom donor photocatalysts in situ generated from benzimidazolium salts and hydride reagents |
| topic | Benzimidazoline and benzimidazolium couple Hydride donor reagent Electron and hydrogen atom donor Reducing photocatalyst Reductive desulfonylation |
| url | http://www.sciencedirect.com/science/article/pii/S2666469023000362 |
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