Ex Situ Generation of Sulfuryl Fluoride for the Synthesis of Aryl Fluorosulfates,Organic Letters

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Ex Situ Generation of Sulfuryl Fluoride for the Synthesis of Aryl Fluorosulfates
Organic Letters ( IF 4.9 ) Pub Date : 2017-09-13 00:00:00 , DOI: 10.1021/acs.orglett.7b02522
Cedrick Veryser ₁ , Joachim Demaerel ₁ , Vidmantas Bieliu̅nas ₁ , Philippe Gilles ₁ , Wim M. De Borggraeve ₁

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A convenient transformation of phenols into the corresponding aryl fluorosulfates is presented: the first protocol to completely circumvent direct handling of gaseous sulfuryl fluoride (SO₂F₂). The proposed method employs 1,1′-sulfonyldiimidazole as a precursor to generate near-stoichiometric amounts of SO₂F₂ gas using a two-chamber reactor. With NMR studies, it was shown that this ex situ gas evolution is extremely rapid, and a variety of phenols and hydroxylated heteroarenes were fluorosulfated in good to excellent yields.

中文翻译：

易地硫酰氟的代芳基Fluorosulfates的合成

提出了将苯酚方便地转化为相应的氟代芳基硫酸盐的方法：完全规避直接处理气态硫酰氟（SO ₂ F ₂）的第一种方法。所提出的方法使用1,1'-磺酰亚胺基咪唑作为前体，通过两腔反应器生成接近化学计量的SO ₂ F ₂气体。通过NMR研究表明，这种非原位气体的释放非常迅速，并且以良好的收率和良好的收率对各种酚和羟基化的杂芳烃进行了氟代硫酸化。

更新日期：2017-09-13

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