N,N′-Di-Boc-N″-fluorosulfonyl-guanidine: A SuFEx-Enabled Guanylating Reagent (SuFEx-G) with Enhanced Reactivity on Water

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-03-20 Epub Date: 2026-03-09 DOI:10.1021/acs.orglett.6c00291

Long Xu, , , Hanzheng Li, , , Meng-Meng Zheng, , , Wang Wei, , , Xiao-Song Xue*, , and , Jiajia Dong*,

引用次数: 0

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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N，N'-Di-Boc-N″-氟磺酰基胍：一种对水具有增强反应活性的SuFEx-G化试剂。

我们报道了N，N'-di-Boc-N″-氟磺酰基胍（SuFEx-G），这是一种具有前所未有的“水上”反应活性的实验稳定的SuFEx-G试剂。在MeCN/H2O中，它与芳香胺、肼和肼形成油滴，加速了boc保护胍类化合物的室温合成，这些化合物可以通过简单的过滤分离出来。机理研究证实了油/水界面对速率加速至关重要，实验和理论数据都表明，由于[NHSO2F]-水解产生的弹簧负载热力学驱动力，SuFEx-G优于Goodman试剂。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.