Metal-free regioselective CH chalcogenylation of coumarins/(hetero)arenes at ambient temperature

Metal-free regioselective CH chalcogenylation of coumarins/(hetero)arenes at ambient temperature

A novel, practical and metal-free approach for the regioselective selenation of coumarins employing (bis(trifluoroacetoxy)iodo)benzene (PIFA) at room temperature is presented. The developed method is suitable for a wide substrate scope and affords 3-selenyl coumarins in good to excellent yields with...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2020-02, Vol.56 (12), p.1847-185
Hauptverfasser: Song, Zengqiang, Ding, Chaochao, Wang, Shaoli, Dai, Qian, Sheng, Yaoguang, Zheng, Zhilong, Liang, Guang
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container_end_page 185
container_issue 12
container_start_page 1847
container_title Chemical communications (Cambridge, England)
container_volume 56
creator Song, Zengqiang
Ding, Chaochao
Wang, Shaoli
Dai, Qian
Sheng, Yaoguang
Zheng, Zhilong
Liang, Guang
description A novel, practical and metal-free approach for the regioselective selenation of coumarins employing (bis(trifluoroacetoxy)iodo)benzene (PIFA) at room temperature is presented. The developed method is suitable for a wide substrate scope and affords 3-selenyl coumarins in good to excellent yields with high selectivity. A radical mechanism is proposed for this new transformation. Furthermore, the application of sulfenylation with coumarines and selenation with other (hetero)arenes in this transformation is successful. A novel and practical method for the direct regioselective chalcogenylation of coumarins at the C3-postion and selenation of other (hetero)arenes has been achieved using PIFA as a promoter at room temperature.
doi_str_mv 10.1039/c9cc09001k
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title Metal-free regioselective CH chalcogenylation of coumarins/(hetero)arenes at ambient temperature
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