(Fluoromethylsulfonyl)methylation of Quinoxalinones Using NaSO2CH2F for C-F Bond Cleavage

We developed a facile, efficient, and scalable route to achieve monofluoromethylsulfinyl alkylation of quinoxalinones. NaSO2CH2F served as the source of methylene to construct new C-C and C-S bonds via C-F bond cleavage. NaSO2CH2F was also the source of SO2CH2F. Density functional theory calculations confirmed the proposed mechanism, in which the SO2CH2F radical is immediately trapped. The reaction exhibited a high level of atom economy. Moreover, some representative products displayed excellent biological activity.

Automated summary

In this study, a facile and efficient approach to achieve monofluoromethylsulfinyl alkylation of quinoxalinones was developed, which involved the construction of new C-C and C-S bonds through the cleavage of C-F bond. The proposed mechanism was confirmed by density functional theory calculations, and the reaction exhibited a high level of atom economy. Moreover, the obtained products showed excellent biological activity.