Sulfur(IV) reagents for the SuFEx-based synthesis of substituted sulfamate esters,Chemical Science

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Sulfur(IV) reagents for the SuFEx-based synthesis of substituted sulfamate esters
Chemical Science ( IF 7.6 ) Pub Date : 2023-01-20 , DOI: 10.1039/d2sc05945b
Kathleen T Downey ₁ , Jia Yi Mo ₁ , Joey Lai ₁ , Brodie J Thomson ₁ , Glenn M Sammis ₁

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Sulfur(VI) fluoride exchange chemistry has been reported to be effective at synthesizing valuable sulfur(VI) functionalities through sequential nucleophilic additions, yet oxygen-based nucleophiles are limited in this approach to phenolic derivatives. Herein, we report a new sulfur(IV) fluoride exchange strategy to access synthetically challenging substituted sulfamate esters from alkyl alcohols and amines. We also report the development of a non-gaseous, sulfur(IV) fluoride exchange reagent, N-methylimidazolium sulfinyl fluoride hexafluorophosphate (MISF). By leveraging the reactivity of the sulfur(IV) center of this novel reagent, the sequential addition of alcohols and amines to MISF followed by oxidation afforded the desired substituted sulfamates in 40–83% yields after two steps. This new strategy expands the scope of SuFEx chemistry by increasing the accessibility of underdeveloped –S(O)F intermediates for future explorations.

中文翻译：

用于基于 SuFEx 合成取代氨基磺酸酯的硫 (IV) 试剂

据报道，硫 ( VI ) 氟化物交换化学可通过顺序亲核加成有效合成有价值的硫 ( VI ) 官能团，但基于氧的亲核试剂在这种方法中仅限于酚类衍生物。在此，我们报告了一种新的硫 ( IV ) 氟化物交换策略，以从烷基醇和胺中获得具有合成挑战性的取代氨基磺酸酯。我们还报告了一种非气态硫 ( IV ) 氟化物交换试剂N-甲基咪唑鎓亚磺酰氟六氟磷酸盐 (MISF) 的开发。通过利用硫的反应性（IV) 作为这种新型试剂的核心，依次将醇和胺添加到 MISF 中，然后氧化，经过两步后得到所需的取代氨基磺酸酯，产率为 40-83%。这种新策略通过增加未开发的-S(O)F 中间体的可及性以供未来探索，从而扩大了 SuFEx 化学的范围。

更新日期：2023-01-20

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