3 years ago

Iron-Catalyzed Radical Decarboxylative Oxyalkylation of Terminal Alkynes with Alkyl Peroxides

Iron-Catalyzed Radical Decarboxylative Oxyalkylation of Terminal Alkynes with Alkyl Peroxides
Yajun Li, Changqing Ye, Xiaotao Zhu, Hongli Bao
An iron-catalyzed oxyalkylation of alkynes with alkyl peroxides as the alkylating reagents has been investigated. Alkyl peroxides are readily available from aliphatic acids and serve simultaneously as the alkylating reagents and internal oxidants. Primary, secondary, and tertiary alkyl groups of aliphatic acids were readily incorporated into C−C triple bonds and diverse α-alkylated ketones were synthesized. Mechanism studies revealed that this reaction involves highly reactive alkyl free radicals. A unique equilibrium between lauric acid and water catalyzed by the iron(III) catalyst was observed. An iron-catalyzed oxyalkylation of alkynes to afford α-alkylated ketones with alkyl peroxides as alkylating reagents was reported. Alkyl peroxides are readily available from aliphatic acids and serve simultaneously as alkylating reagents and internal oxidants. Synthetic applications and mechanism studies were conducted(see scheme).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701830

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