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Fe-Catalyzed decarbonylative alkylation–peroxidation of alkenes with aliphatic aldehydes and hydroperoxide under mild conditions

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Abstract

A convenient Fe-catalyzed decarbonylative alkylation–peroxidation of alkenes with aliphatic aldehydes and TBHP to provide chain elongated peroxides is developed, which is further applied to the one-pot synthesis of alkylated ketones. Aliphatic aldehydes were decarbonylated into 1°, 2° and 3° alkyl radicals at low temperature which subsequently allows the cascade construction of C(sp3)–C(sp3) and C(sp3)–O bonds via radical insertion and radical–radical coupling. Various alkenes including mono-substituted, terminally disubstituted or internally disubstituted styrenes bearing synthetically useful functional groups and electron-poor acrylates were tolerated.

Graphical abstract: Fe-Catalyzed decarbonylative alkylation–peroxidation of alkenes with aliphatic aldehydes and hydroperoxide under mild conditions

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Publication details

The article was received on 06 Sep 2018, accepted on 28 Nov 2018 and first published on 29 Nov 2018


Article type: Paper
DOI: 10.1039/C8GC02834F
Citation: Green Chem., 2019, Advance Article
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    Fe-Catalyzed decarbonylative alkylation–peroxidation of alkenes with aliphatic aldehydes and hydroperoxide under mild conditions

    C. Wu, R. Li, Q. Wang and L. Yang, Green Chem., 2019, Advance Article , DOI: 10.1039/C8GC02834F

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