A Convenient One-Pot Process for Converting Thiols into Sulfonyl Fluorides Using H2O2 as an Oxidant

Synthesis Pub Date : 2024-07-19 DOI:10.1055/s-0043-1775384
Guang Tao, Eman Fayad, Ola A. Abu Ali, Bright Oyom, Hua-Li Qin
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Abstract

A novel protocol for synthesizing sulfonyl fluorides from thiols in one pot is reported. Utilizing SOCl2 and H2O2 as low-cost and convenient reagents allows the direct oxidative chlorination of readily available thiol derivatives to give the corresponding sulfonyl chlorides, with subsequent fluoride–chloride exchange mediated by KHF2 giving access to the desired sulfonyl fluorides. This transformation features mild conditions, operational simplicity and high efficiency, and utilizes a broad substrate scope, including a variety of aryl, alkyl, benzyl and heteroaryl thiols.

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使用 H2O2 作为氧化剂将硫醇转化为磺酰氟的便捷式单锅工艺
本报告介绍了一种以硫醇为原料一锅合成磺酰氟的新方法。利用 SOCl2 和 H2O2 作为低成本且方便的试剂,可以直接氧化氯化现成的硫醇衍生物,得到相应的磺酰基氯,随后在 KHF2 的介导下进行氟氯交换,得到所需的磺酰氟。这种转化方法条件温和、操作简单、效率高,而且底物范围广泛,包括各种芳基、烷基、苄基和杂芳基硫醇。
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