<i>N</i> , <i>N</i> ′-Di-Boc- <i>N</i> ″-fluorosulfonyl-guanidine: A SuFEx-Enabled Guanylating Reagent (SuFEx-G) with Enhanced Reactivity on Water
We report N,N'-di-Boc-N″-fluorosulfonyl-guanidine (<b>SuFEx-G</b>), a bench-stable SuFEx-enabled guanylating reagent with unprecedented "on-water" reactivity. In MeCN/H<sub>2</sub>O, 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 <b>SuFEx-G</b> outperforms Goodman's reagent due to the spring-loaded thermodynamic driving force from [NHSO<sub>2</sub>F]<sup><b>-</b></sup> hydrolysis.
Authors
- X.D. Xue (ORCID: https://orcid.org/0000-0002-3267-0290)
- M. R. Zheng
- Long Xu (ORCID: https://orcid.org/0009-0006-9035-0769)
- Hanzheng Li
- Jiajia Dong
- Wang Wei
Institutions
- Shanghai Jiao Tong University (CN)
- Chinese Academy of Sciences (CN)
- Shanghai Institute of Organic Chemistry (CN)
- Center for Translational Molecular Medicine (NL)
- Institute of Natural Science (KP)
- University of Chinese Academy of Sciences (CN)
- RE Hydrogen (United Kingdom) (GB)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-03-09
- DOI
- https://doi.org/10.1021/acs.orglett.6c00291
- Primary Topic
- Chemical Synthesis and Analysis
- Type
- article
- Field-Weighted Citation Impact
- 0.00