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

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 r...

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Published inGreen chemistry : an international journal and green chemistry resource : GC Vol. 21; no. 2; pp. 269 - 274
Main Authors Wu, Chuan-Shuo, Li, Rong, Wang, Qi-Qiang, Yang, Luo
Format Journal Article
LanguageEnglish
Published Cambridge Royal Society of Chemistry 2019
Subjects
Acrylates
Aldehydes
Aliphatic compounds
Alkenes
Alkylation
Functional groups
Green chemistry
Iron
Ketones
Low temperature
Peroxidation
Peroxides
Styrenes
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Summary: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(sp 3 )–C(sp 3 ) and C(sp 3 )–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.
ISSN:1463-9262
1463-9270
DOI:10.1039/C8GC02834F