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Iron‐Catalyzed Radical Decarboxylative Oxyalkylation of Terminal Alkynes with Alkyl Peroxides
Author(s) -
Zhu Xiaotao,
Ye Changqing,
Li Yajun,
Bao Hongli
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701830
Subject(s) - alkyl , chemistry , catalysis , reagent , alkylation , primary (astronomy) , organic chemistry , decarboxylation , radical , lauric acid , medicinal chemistry , fatty acid , physics , astronomy
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.