Related Experiment Video
Updated: Jun 29, 2025

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
N-Fluorosulfonyl Guanidine: An Entry to N-Guanyl Sulfamides and Sulfamates
Wei Wang1,2,3, Jingyuan Li4, Long Xu1
1Institute of Translational Medicine, National Facility for Translational Medicine (Shanghai), Shanghai Jiao Tong University, Shanghai 200240, China.
Abstract:
Here, we present the straightforward synthesis of N-fluorosulfonyl guanidine (1) from two industrial feedstocks, guanidine hydrochloride and sulfuryl fluoride (SO2F2), using SuFEx chemistry. Compound 1 exhibits excellent stability under ambient conditions and displays unique SuFEx reactivity toward amines and phenols to generate N-guanyl sulfamides and sulfamates that have rarely been accessed. Notably, water serves as an effective solvent in this process. Our protocol provides a reliable pathway for the synthesis and investigation of these novel guanidine-containing molecules.
More Related Videos
09:04A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
08:46Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
Published on: July 26, 2018
Related Concept Videos
Amines to Sulfonamides: The Hinsberg Test
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing...
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Phase II Reactions: Sulfation and Conjugation with α-Amino Acids
Phase II Reactions: Glucuronidation
Drug Metabolism: Phase II Reactions
Preparation and Reactions of Sulfides