Bench-Stable Transfer Reagent Facilitates the Generation of Trifluoromethyl-sulfonimidamides

J Org Chem. 2018 Aug 17;83(16):9510-9516. doi: 10.1021/acs.joc.8b01244. Epub 2018 Jul 6.

Abstract

Sulfonimidamides are an emerging bioisosteric replacement in medicinal chemistry projects, and therefore new chemistries are necessary to access this functionality. The general synthesis of CF3-sulfonimidamides from an activated bench-stable transfer reagent is described. A diverse reaction scope is demonstrated, with a wide range of nucleophilic amines being tolerated in this transformation. The CF3-sulfonimidamides obtained contain an additional diversity point, in the form a protected imine, that could be unmasked to allow late stage modifications.