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Updated: Mar 10, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
N,N'-Di-Boc-N″-fluorosulfonyl-guanidine: A SuFEx-Enabled Guanylating Reagent (SuFEx-G) with Enhanced Reactivity on
Long Xu1, Hanzheng Li2, Meng-Meng Zheng3,4
1Institute of Translational Medicine, National Facility for Translational Medicine (Shanghai), Shanghai Jiao Tong University, Shanghai 200240, China.
Abstract:
We report N,N'-di-Boc-N″-fluorosulfonyl-guanidine (SuFEx-G), a bench-stable SuFEx-enabled guanylating reagent with unprecedented "on-water" reactivity. In MeCN/H2O, it forms oil droplets with aromatic amines, hydrazines, and hydrazides, accelerating room-temperature synthesis of Boc-protected guanidines that can be isolated by simple filtration. Mechanistic studies confirm oil/water interfaces essential for rate acceleration, and both experimental and theoretical data show SuFEx-G outperforms Goodman's reagent due to the spring-loaded thermodynamic driving force from [NHSO2F]- hydrolysis.
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