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Metal-free regioselective C–H chalcogenylation of coumarins/(hetero)arenes at ambient temperature

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Abstract

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.

Graphical abstract: Metal-free regioselective C–H chalcogenylation of coumarins/(hetero)arenes at ambient temperature

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Article information


Submitted
19 Nov 2019
Accepted
10 Jan 2020
First published
11 Jan 2020

Chem. Commun., 2020, Advance Article
Article type
Communication

Metal-free regioselective C–H chalcogenylation of coumarins/(hetero)arenes at ambient temperature

Z. Song, C. Ding, S. Wang, Q. Dai, Y. Sheng, Z. Zheng and G. Liang, Chem. Commun., 2020, Advance Article , DOI: 10.1039/C9CC09001K

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