Abstract

Useful and applicable methods for one-pot and odorless synthesis of unsymmetrical and symmetrical diaryl sulfides via C–O bond activation are presented. First, a new efficient procedure for the synthesis of unsymmetrical sulfides using the cross-coupling reaction of phenolic esters such as acetates, tosylates, and triflates and with arylboronic acid or triphenyltin chloride as the coupling partners is reported. Depending on the reaction, S₈/KF or S₈/NaOt-Bu system is found to be an effective source of sulfur in the presence of copper salts and in poly(ethylene glycol) as a green solvent. Then, the synthesis of symmetrical diaryl sulfides from phenolic compounds by using S₈ as the sulfur source and NaOt-Bu in anhydrous DMF at 120 °C under N₂ is described. By these protocols, the synthesis of a variety of unsymmetrical and symmetrical sulfides become easier than the available protocols in which thiols and aryl halides are directly used for the preparation of the sulfides.

Useful and applicable methods for one-pot and odorless synthesis of unsymmetrical and symmetrical diaryl sulfides via C–O bond activation are presented. First, a new efficient procedure for the synthesis of unsymmetrical sulfides using the cross-coupling reaction of phenolic esters such as acetates, tosylates, and triflates and with arylboronic acid or triphenyltin chloride as the coupling partners is reported. Depending on the reaction, S₈/KF or S₈/NaOt-Bu system is found to be an effective source of sulfur in the presence of copper salts and in poly(ethylene glycol) as a green solvent. Then, the synthesis of symmetrical diaryl sulfides from phenolic compounds by using S₈ as the sulfur source and NaOt-Bu in anhydrous DMF at 120 °C under N₂ is described. By these protocols, the synthesis of a variety of unsymmetrical and symmetrical sulfides become easier than the available protocols in which thiols and aryl halides are directly used for the preparation of the sulfides.

中文翻译：

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以S8为硫源时，通过C–O键的裂解，形成铜催化的C–S键的形成

摘要

提出了一种有用且适用的通过C–O键活化一锅无味合成不对称和对称二芳基硫化物的方法。首先，报道了一种新的有效方法，用于合成不对称硫化物，该方法使用酚酯（如乙酸酯，甲苯磺酸酯和三氟甲磺酸酯）的交叉偶联反应，并以芳基硼酸或三苯基氯化锡为偶联伙伴。取决于反应，发现S ₈ / KF或S ₈ / NaO t -Bu体系在铜盐存在下和在聚乙二醇中作为绿色溶剂是硫的有效来源。然后，以S ₈为硫源和NaO t由酚类化合物合成对称的二芳基硫醚描述了在N ₂下在120°C的无水DMF中的-Bu 。通过这些方案，与不直接将硫醇和芳基卤化物用于制备硫化物的现有方案相比，各种不对称和对称硫化物的合成变得更加容易。

提出了一种有用且适用的通过C–O键活化一锅无味合成不对称和对称二芳基硫化物的方法。首先，报道了一种新的有效方法，用于合成不对称硫化物，该方法使用酚酯（如乙酸酯，甲苯磺酸酯和三氟甲磺酸酯）的交叉偶联反应，并以芳基硼酸或三苯基氯化锡为偶联伙伴。取决于反应，发现S ₈ / KF或S ₈ / NaO t -Bu体系在铜盐存在下和在聚乙二醇中作为绿色溶剂是硫的有效来源。然后，以S ₈为硫源和NaO t由酚类化合物合成对称的二芳基硫醚描述了在N ₂下在120°C的无水DMF中的-Bu 。通过这些方案，与不直接将硫醇和芳基卤化物用于制备硫化物的现有方案相比，各种不对称和对称硫化物的合成变得更加容易。