Metal-Free Arylation of Ethyl Acetoacetate with Hypervalent Diaryliodonium Salts: an Immediate Access to Diverse 3- Aryl-4(1H)-Quinolones

24 Feb 2015

Andrii Monastyrskyi, Niranjan K. Namelikonda, and Roman Manetsch

Journal of Organic Chemistry

doi: 10.1021/jo5023958


A clean arylation protocol of ethyl acetoacetate was developed using hypervalent diaryliodonium salts under mild and metal-free conditions. The scope of the reaction, using symmetric and unsymmetric iodonium salts with varying sterics and electronics was examined. Further, this method has been applied for the synthesis of antimalarial compound ELQ-300, which is currently in preclinical development.

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