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DABCO‐promoted Diaryl Thioether Formation by Metal‐catalyzed Coupling of Sodium Sulfinates and Aryl Iodides
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2020-03-24 , DOI: 10.1002/adsc.202000221
Yanpeng Liu 1 , Long Yin Lam 1 , Jiqing Ye 1 , Nicolas Blanchard 2 , Cong Ma 1
Affiliation  

A scalable catalytic synthesis method using commodity chemicals for constructing diaryl thioethers directly from sodium arylsulfinates and iodoarenes is reported in this study. In the presence of CuO or other copper salts such as Cu(OAc)2 as well as palladium catalysts, DABCO demonstrated to be essential to promote this transformation. Various iodoarenes and aryl sulfinates were examined and demonstrated the viability of this method. The mechanistic study showed that radical reactions occurred, while DABCO N ‐oxide radical can be observed by mass spectrometry. A plausible catalytic mechanism involving DABCO is also discussed, suggesting synergistic reduction of sulfinate by Cu(II) and DABCO is the key step of this coupling reaction.

中文翻译:

DABCO通过亚磺酸钠和碘代碘化物的金属催化偶联促进二芳基硫醚的形成

这项研究报道了使用商品化学品直接从芳基亚磺酸钠和碘芳烃构建二芳基硫醚的可扩展催化合成方法。在CuO或其他铜盐(例如Cu(OAc)2)以及钯催化剂的存在下,DABCO被证明对促进这种转变至关重要。检查了各种碘代芳烃和芳基亚磺酸盐,证明了该方法的可行性。机理研究表明发生了自由基反应,而质谱可以观察到DABCO N-氧化物自由基。还讨论了涉及DABCO的可能的催化机理,表明亚铜(II)和DABCO协同还原亚磺酸盐是该偶联反应的关键步骤。
更新日期:2020-03-24
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