Selectivity Controlled Hydroamination of Alkynes to SulfonylFluoride Hubs: Development and Application

A hydroamination of unactivated alkynes andlithium bis(fluorosulfonyl)imide (LiN(SO2F)2)isdescribedunder mild conditions, affording a single regioisomer of thesulfonylfluorides. This method features broad functional groupcompatibility and delivers the target vinylfluorosulfonimides ingood to excellent yields. Moreover, gram-scale hydroamination ofterminal and internal alkynes is achieved. Further transformations exploiting the reactivity of the vinylfluorosulfonimide aresubsequently developed for the synthesis offluorosulfates and diphenyl sulfate

Automated summary

This paper describes a hydroamination reaction of unactivated alkynes and lithium bis(fluorosulfonyl)imide under mild conditions, resulting in a single regioisomer of sulfonylfluorides. The method shows broad functional group compatibility and high yields of the target vinylfluorosulfonimides. Additionally, gram-scale hydroamination of both terminal and internal alkynes has been achieved, and further transformations of the vinylfluorosulfonimide have been developed for the synthesis of fluorosulfates and diphenyl sulfate.