Room-Temperature Arylation of Thiols: Breakthrough with Aryl Chlorides
Room-Temperature Arylation of Thiols: Breakthrough with Aryl Chlorides
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硫醇的室温芳基化：芳基氯的突破
DOI：
10.1002/anie.201610414
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发表时间：
2017-01-16
影响因子：
16.6
通讯作者：
Fu, Hua
中科院分区：
文献类型：
--
作者：
Jiang, Min;Li, Haifang;Fu, Hua
芳基C-S键的形成是重要的化学转化，因为芳基硫醚是合成生物和药物活性分子和有机材料的有价值的结构单元。芳基硫醚传统上是通过过渡金属催化的芳基卤与硫醇的交叉偶联来合成的。然而，使用的芳基卤化物通常是溴化物和碘化物;容易获得的低成本芳基氯化物通常不够反应性。此外，硫醇使过渡金属催化剂失活，迫使化学家使用高催化剂负载量、特别设计的配体、高温和/或强碱，从而导致高成本和某些官能团的不相容性。在此，我们描述了一个简单而有效的可见光光氧化还原芳基化硫醇与芳基卤化物在室温下。更重要的是，各种芳基氯在本条件下也是有效的芳基化试剂。
The formation of aryl C-S bonds is an important chemical transformation because aryl sulfides are valuable building blocks for the synthesis of biologically and pharmaceutically active molecules and organic materials. Aryl sulfides have traditionally been synthesized through the transition-metal-catalyzed cross-coupling of aryl halides with thiols. However, the aryl halides used are usually bromides and iodides; readily available, low-cost aryl chlorides often not reactive enough. Furthermore, the deactivation of transition-metal catalysts by thiols has forced chemists to use high catalyst loadings, specially designed ligands, high temperatures, and/or strong bases, thus leading to high costs and the incompatibility of some functional groups. Herein, we describe a simple and efficient visible-light photoredox arylation of thiols with aryl halides at room temperature. More importantly, various aryl chlorides are also effective arylation reagents under the present conditions.