Iron-catalyzed peroxidation-carbamoylation of alkenes with hydroperoxides and formamides via formyl C(sp 2 )-H functionalization

A reaction protocol in which FeCl and tert-butyl hydroperoxide facilitated a selective radical coupling reaction of aryl alkenes or 1,3-enynes with tert-butyl hydroperoxide and formamides to prepare an array of β-peroxy amides has been achieved. The β-peroxy amide could serve as a synthetic precurso...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2017, Vol.53 (95), p.12830-12833
Main Authors: Cheng, Jun-Kee, Shen, Liang, Wu, Liu-Hai, Hu, Xu-Hong, Loh, Teck-Peng
Format: Article
Language:English
Subjects:
Alkenes
Amides
Aromatic compounds
Butyl hydroperoxide
Iron chlorides
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Summary:A reaction protocol in which FeCl and tert-butyl hydroperoxide facilitated a selective radical coupling reaction of aryl alkenes or 1,3-enynes with tert-butyl hydroperoxide and formamides to prepare an array of β-peroxy amides has been achieved. The β-peroxy amide could serve as a synthetic precursor which was facilely converted to β-hydroxy amide, β-keto amide and β-lactam following subsequent chemical transformation.
ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc08074c