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Iron-Facilitated Oxidative Radical Decarboxylative Cross-Coupling between α-Oxocarboxylic Acids and Acrylic Acids: An Approach to α,β-Unsaturated Carbonyls

Qing Jiang, Jing Jia, Bin Xu, An Zhao and Can-Cheng Guo*

*College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China, Email:

Q. Jiang, J. Jia, B. Xu, A. Zhao, C.-C. Guo, J. Org. Chem., 2015, 80, 3586-3596.

DOI: 10.1021/acs.joc.5b00267

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A Fe-mediated decarboxylative cross-coupling reaction between α-oxocarboxylic acids and acrylic acids in aqueous solution provides an efficient and expeditious approach to α,β-unsaturated carbonyl compounds. This transformation offers a wide substrate scope and good functional group compatibility utilizing inexpensive and easily accessible reagents. Mechanism studies suggest that a free radical pathway is involved.

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Key Words

enones, potassium peroxydisulfate

ID: J42-Y2015