An Easy, General and Practical Method for the Construction of Alkyl Sulfonyl Fluorides,Advanced Synthesis & Catalysis

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An Easy, General and Practical Method for the Construction of Alkyl Sulfonyl Fluorides
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-06-15 , DOI: 10.1002/adsc.202000515
Xu Zhang ₁ , Wan‐Yin Fang ₁ , Ravindar Lekkala ₁ , Wenjian Tang ₂ , Hua‐Li Qin ₁

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A visible light‐induced reductive addition of 1°, 2° and 3° alkyl iodides to ethenesulfonyl fluoride, employing Hantzsch ester as a hydrogen source at room temperature was developed. This method featured a wide substrate scope and great functional group compatibility, providing facile and robust process to alkyl sulfonyl fluorides including enzyme inhibitors, natural products and drugs derivatives in up to 99% yield. Further derivatization of resultant aliphatic sulfonyl fluorides was also achieved through sulfur fluoride exchange (SuFEx) reactions to deliver sulfonates and sulfonamides as privileged motifs for medicinal chemistry.

中文翻译：

一种简便，通用和实用的烷基磺酰氟的构建方法

在室温下，使用汉茨sch酯作为氢源，开发了一种可见光诱导的将1°，2°和3°烷基碘还原加入乙磺酰氟的方法。该方法具有广泛的底物范围和出色的官能团相容性，可为烷基磺酰氟（包括酶抑制剂，天然产物和药物衍生物）提供简便而稳固的工艺，产率高达99％。还可以通过氟化硫交换（SuFEx）反应实现对生成的脂肪族磺酰氟的进一步衍生，以传递磺酸盐和磺酰胺作为药物化学的优先基序。

更新日期：2020-08-19

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