Regioselective Synthesis of Selenide Ethers through a Decarboxylative Coupling Reaction

An efficient and selective approach to the synthesis of selenide ethers containing one or two geminal C–Se bonds from readily available diselenides and phenylacetic acids was developed. Compounds containing one C–Se bond were prepared by employing air as the oxidant under metal‐free conditions, wher...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2017-11, Vol.359 (22), p.3950-3961
Main Authors: Cui, Fei‐Hu, Chen, Jing, Su, Shi‐Xia, Xu, Yan‐li, Wang, Heng‐shan, Pan, Ying‐ming
Format: Article
Language:English
Subjects:
Cesium
Chemical bonds
Chemical synthesis
decarboxylative coupling reaction
diselenides
Ethers
phenylacetic acid
Regioselectivity
selenide ethers
Selenides
Selenium
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Summary:An efficient and selective approach to the synthesis of selenide ethers containing one or two geminal C–Se bonds from readily available diselenides and phenylacetic acids was developed. Compounds containing one C–Se bond were prepared by employing air as the oxidant under metal‐free conditions, whereas compounds having two geminal C–Se bonds were formed via the iron(III) chloride/oxygen/cesium carbonate (FeCl3/O2/Cs2CO3) system. Moreover, 1,2‐diphenyldisulfane also could be smoothly converted into the corresponding sulfur ether product under the standard reaction conditions.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201700676