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An Iodide-Mediated Transition-Metal-Free Strategy towards Unsymmetrical Diaryl Sulfides via Arylhydrazines and Thiols
Synthesis ( IF 2.2 ) Pub Date : 2019-11-25 , DOI: 10.1055/s-0039-1690757
Farnaz Jafarpour , Mohammad Asadpour , Meysam Azizzade , Mehran Ghasemi , Saideh Rajai-Daryasarei

A mild, scalable iodine-mediated oxidative cross-coupling reaction of arylhydrazines and thiols for construction of thioethers (sulfides) in the absence of any transition metals or photocatalysts is disclosed. A variety of unsymmetrical diaryl sulfides with broad substrate scope both on thiols and hydrazines were synthesized in high yields in water at room temperature. Furthermore, to demonstrate the utility of the protocol, the above C–S bond formation was applied in the synthesis of the key structure of vortioxetine as an antidepressant drug. The gram-scale outcome also added to the potential utility of this protocol.

中文翻译:

通过芳基肼和硫醇实现不对称二芳基硫醚的碘化物介导的无过渡金属的策略

公开了在不存在任何过渡金属或光催化剂的情况下,温和的,可扩展的碘介导的芳基肼和硫醇的氧化交叉偶联反应,用于构建硫醚(硫化物)。在室温下于水中以高收率合成了多种在硫醇和肼上具有广泛底物范围的不对称二芳基硫醚。此外,为了证明该方案的实用性,上述C–S键的形成被应用于伏替西汀作为抗抑郁药的关键结构的合成中。克级结果也增加了该协议的潜在用途。
更新日期:2019-11-26
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