Selectivity Controlled Hydroamination of Alkynes to Sulfonyl Fluoride Hubs: Development and Application.

Abstract

A hydroamination of unactivated alkynes and lithium bis(fluorosulfonyl)imide (LiN(SO2F)2) is described under mild conditions, affording a single regioisomer of the sulfonyl fluorides. This method features broad functional group compatibility and delivers the target vinyl fluorosulfonimides in good to excellent yields. Moreover, gram-scale hydroamination of terminal and internal alkynes is achieved. Further transformations exploiting the reactivity of the vinyl fluorosulfonimide are subsequently developed for the synthesis of fluorosulfates and diphenyl sulfate.