Transition-Metal-Free HFIP-Mediated Organo Chalcogenylation of Arenes/Indoles with Thio-/Selenocyanates

We have developed a protocol for the synthesis of diaryl thio-/selenoethers by the reaction of aryl chalcogenocyanates with electron rich arenes/hetero arenes via HFIP promoted C–H activation. The reaction produces chalcogenides in good to excellent yields under mild conditions without the need of a...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-07, Vol.86 (14), p.9317-9327
Main Authors: Kalaramna, Pratibha, Goswami, Avijit
Format: Article
Language:English
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Summary:We have developed a protocol for the synthesis of diaryl thio-/selenoethers by the reaction of aryl chalcogenocyanates with electron rich arenes/hetero arenes via HFIP promoted C–H activation. The reaction produces chalcogenides in good to excellent yields under mild conditions without the need of a transition metal as a catalyst. The HFIP-mediated reactions tolerated a wide range of functional groups and set the stage for the synthesis of diversely decorated chalcogenides. A mechanism involving activation of the C–H bond through hydrogen bonding is proposed.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c00478