Fluorosulfates and sulfamoyl fluorides are versatile functional groups that have been used in a myriad of applications ranging from chemical biology to cross-coupling. While the state-of-the-art protocols to access fluorosulfates and sulfamoyl fluorides rely on the use of toxic sulfuryl fluoride gas, an easily weighable solid reagent would facilitate the synthesis of these functional groups. Towards this end, we report the invention of AISF ([4-(Acetylamino)phenyl]ImidodiSulfuryl diFluoride) a convenient, shelf-stable, crystalline reagent for the synthesis of fluorosulfates and sulfamoyl fluorides. We highlight the broad functional group and reagent compatibility of AISF, showcase single-flask cross-couplings and other reactions of phenols via the intermediacy of the AISF-generated fluorosulfate and demonstrate the selective functionalization of a tyrosine residue on a peptidic macrocycle under biologically relevant aqueous conditions.

Development of a crystalline, shelf-stable reagent for the synthesis of fluorosulfates and sulfamoyl fluorides

256th National Meeting (2018)

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