33122-25-7Relevant academic research and scientific papers
Iron-Catalyzed Asymmetric Decarboxylative Azidation
Wang, Kaikai,Li, Yajun,Li, Xiaoyan,Li, Daliang,Bao, Hongli
supporting information, p. 8847 - 8851 (2021/11/24)
The first iron-catalyzed asymmetric azidation of benzylic peresters has been reported with trimethylsilyl azide (TMSN3) as the azido source. Hydrocarbon radicals that lack of strong interactions were capable to be enantioselectively azidated. The reaction features good functional group tolerance, high yields, and mild conditions. The chiral benzylic azides can further be used in click reaction, phosphoramidation, and reductive amination, which demonstrate the synthetic values of this reaction.
Fluorine transfer to alkyl radicals
Rueda-Becerril, Montserrat,Chatalova Sazepin, Claire,Leung, Joe C. T.,Okbinoglu, Tulin,Kennepohl, Pierre,Paquin, Jean-Francois,Sammis, Glenn M.
supporting information; experimental part, p. 4026 - 4029 (2012/04/10)
The development of new synthetic technologies for the selective fluorination of organic compounds has increased with the escalating importance of fluorine-containing pharmaceuticals. Traditional methods potentially applicable to drug synthesis rely on the use of ionic forms of fluorine (F - or F+). Radical methods, while potentially attractive as a complementary approach, are hindered by a paucity of safe sources of atomic fluorine (F?). A new approach to alkyl fluorination has been developed that utilizes the reagent N-fluorobenzenesulfonimide as a fluorine transfer agent to alkyl radicals. This approach is successful for a broad range of alkyl radicals, including primary, secondary, tertiary, benzylic, and heteroatom-stabilized radicals. Furthermore, calculations reveal that fluorine-containing ionic reagents are likely candidates for further expansion of this approach to polar reaction media. The use of these reagents in alkyl radical fluorination has the potential to enable powerful new transformations that otherwise would take multiple synthetic steps.
