35076-77-8Relevant articles and documents
The copper-catalyzed ring-opening reactions of cyclopropanes by N-fluorobenzenesulfonimide toward N-allylsulfonamides
Zhou, Aijun,Shao, Ying,Chen, Fan,Qian, Peng-Cheng,Cheng, Jiang
supporting information, (2022/01/03)
In this paper, we reported a copper-catalyzed ring-opening reaction of arylcyclopropanes by N-fluorobenzenesulfonimide, leading to N-allylsulfonamides in moderate to good yields. This procedure tolerated bromo, fluoro, trifluoromethyl, phenyl and alkyl groups in the phenyl, proceeding with a sequential ring-opening of arylcyclopropanes, and copper-mediated β-H elimination of alkyl radical.
Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations
Svec, Riley L.,Hergenrother, Paul J.
supporting information, p. 1857 - 1862 (2019/12/27)
Diazomethane is one of the most versatile reagents in organic synthesis, but its utility is limited by its hazardous nature. Although alternative methods exist to perform the unique chemistry of diazomethane, these suffer from diminished reactivity and/or correspondingly harsher conditions. Herein, we describe the repurposing of imidazotetrazines (such as temozolomide, TMZ, the standard of care for glioblastoma) for use as synthetic precursors of alkyl diazonium reagents. TMZ was employed to conduct esterifications and metal-catalyzed cyclopropanations, and results show that methyl ester formation from a wide variety of substrates is especially efficient and operationally simple. TMZ is a commercially available solid that is non-explosive and non-toxic, and should find broad utility as a replacement for diazomethane.
