Full metadata record
DC Field | Value | Language |
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dc.contributor.author | Shunichi Fukuzumi | - |
dc.date.accessioned | 2024-05-20T16:31:12Z | - |
dc.date.available | 2024-05-20T16:31:12Z | - |
dc.date.issued | 2024 | - |
dc.identifier.issn | 2155-5435 | - |
dc.identifier.other | OAK-34885 | - |
dc.identifier.uri | https://dspace.ewha.ac.kr/handle/2015.oak/268452 | - |
dc.description.abstract | 9-(2,6-Dimethylphenyl)-10-methylacridinium perchlorate ([Acr+-Xyl]ClO4-), 9-(4-chloro-2,6-dimethylphenyl)-10-methylacridinium perchlorate ([Acr+-XylCl]ClO4-), and 9-(4-fluoro-2,6-dimethylphenyl)-10-methylacridinium perchlorate ([Acr+-XylF]ClO4-) were synthesized by the Grignard reaction. The one-electron reduction potentials (Ered vs SCE) of Acr+-Xyl, Acr+-XylCl, and Acr+-XylF in deaerated acetonitrile (MeCN) were determined by cyclic voltammetry to be nearly the same as −0.55, −0.53, and −0.53 V, respectively. On the other hand, the one-electron oxidation potentials (Eox vs SCE) of Acr+-Xyl, Acr+-XylF, and Acr+-XylCl were determined by the second-harmonic alternative current voltammetric method to be +2.15, +2.20, and +2.21 V, respectively. The Eox value of Acr+-XylCl is higher than the Eox value of toluene (+2.20 V). Thus, photocatalytic oxygenation of toluene with oxygen occurs efficiently via electron transfer from toluene to the XylCl•+ moiety of the triplet electron-transfer state of Acr+-XylCl under photoirradiation of Acr+-XylCl in oxygen-saturated MeCN. By contrast, no oxygenation of toluene occurred with the 9-mesityl-10-methylacridinium ion (Acr+-Mes) used as a photocatalyst due to the lack of oxidizing ability to oxidize toluene. The metal-free trifluoromethylation of toluene derivatives has also been made possible by using Acr+-XylCl as a photocatalyst and S-(trifluoromethyl)dibenzothiophenium (CF3DBT+) as a trifluoromethyl source. The photocatalytic reaction mechanism was clarified by transient absorption and electrochemical measurements. © 2024 The Authors. Published by American Chemical Society. | - |
dc.language | English | - |
dc.publisher | American Chemical Society | - |
dc.subject | acridinium | - |
dc.subject | C-H activation | - |
dc.subject | electron transfer | - |
dc.subject | organocatalyst | - |
dc.subject | photooxygenation | - |
dc.subject | photoredox catalyst | - |
dc.subject | radical | - |
dc.subject | trifluoromethylation | - |
dc.title | 9-(4-Halo-2,6-xylyl)-10-methylacridinium Ion as an Effective Photoredox Catalyst for Oxygenation and Trifluoromethylation of Toluene Derivatives | - |
dc.type | Article | - |
dc.relation.issue | 4 | - |
dc.relation.volume | 14 | - |
dc.relation.index | SCIE | - |
dc.relation.index | SCOPUS | - |
dc.relation.startpage | 2671 | - |
dc.relation.lastpage | 2684 | - |
dc.relation.journaltitle | ACS Catalysis | - |
dc.identifier.doi | 10.1021/acscatal.3c06111 | - |
dc.identifier.wosid | WOS:001163381200001 | - |
dc.identifier.scopusid | 2-s2.0-85185286942 | - |
dc.author.google | Ohkubo | - |
dc.author.google | Kei | - |
dc.author.google | Matsumoto | - |
dc.author.google | Soichiro | - |
dc.author.google | Asahara | - |
dc.author.google | Haruyasu | - |
dc.author.google | Fukuzumi | - |
dc.author.google | Shunichi | - |
dc.contributor.scopusid | Shunichi Fukuzumi(35430038100;58409757400) | - |
dc.date.modifydate | 20240520131921 | - |