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Published on: November 9, 2019
B2Pin2-enabled reductive thioesterification of aryl triflates with thiocarbonates
Houguang Shi1,2, Fan Wu3, Wei Zhu2
1School of Medicine, Shanghai University, Shanghai 200444, China. hegui_gong@shu.edu.cn.
Abstract:
In this work, we demonstrate a B2Pin2-mediated reductive coupling of aryl triflates with thiocarbonates for aryl thioester synthesis. This method surpasses previous Zn-based protocols, especially for pyridyl and sterically hindered 2,6-disubstituted arenes, likely due to distinct reduction pathways. Its utility is demonstrated in the thioesterification of pharmaceuticals (apixaban, ezetimibe, ethinyl estradiol derivatives) under mild conditions. Furthermore, this work lays the foundation for B2Pin2-driven reductive C(sp2)-C(sp2) couplings using earth-abundant metals, offering a scalable alternative to traditional Zn/Mn reductants in industrial settings.
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