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Desulfonylative Radical Truce–Smiles Rearrangement Utilizing the Benzimidazoline and Benzimidazolium Redox Couple
Synlett ( IF 1.7 ) Pub Date : 2023-09-19 , DOI: 10.1055/a-2153-6594
Ryo Miyajima 1 , Manon Okamura 1 , Kazuki Oomori 1 , Hajime Iwamoto 1 , Kan Wakamatsu 2 , Eietsu Hasegawa 3
Affiliation  

We have developed protocols for promoting redox reactions utilizing the 2-substituted 1,3-dimethylbenzimidazoline (BIH–R) and benzimidazolium (BI+–R) couples which were applied to the desulfonylative radical Truce–Smiles rearrangement. Expected rearrangement products formed in modest to good yields in these processes, in which added or in situ generated BIH–R serve as electron- and hydrogen-atom-donating reagents or photocatalysts. DFT calculations were carried out to gain the information about the radical intermediates involved in the rearrangement reaction.



中文翻译:

利用苯并咪唑啉和苯并咪唑鎓氧化还原对进行脱磺基自由基休战-微笑重排

我们开发了利用 2-取代 1,3-二甲基苯并咪唑啉 (BIH–R) 和苯并咪唑鎓 (BI + –R) 对促进氧化还原反应的方案,并将其应用于去磺酰基自由基 Truce–Smiles 重排。在这些过程中,预期的重排产物以中等至良好的产率形成,其中添加或原位生成的 BIH-R 作为电子和氢原子供给试剂或光催化剂。进行DFT计算以获得重排反应中涉及的自由基中间体的信息。

更新日期:2023-09-20
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