DOI: 10.1055/a-2153-6594 ISSN:
Desulfonylative Radical Truce-Smiles Rearrangement Utilizing the Benzimidazoline and Benzimidazolium Redox Couple
Ryo Miyajima, Manon Okamura, Kazuki Oomori, Hajime Iwamoto, Kan Wakamatsu, Eietsu Hasegawa- Organic Chemistry
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.