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Synthesis of Ethyl Arylpropiolates through Palladium-Catalyzed Cross-Coupling­ Reactions of Aryl Iodides with In Situ Generated Lithium Tetrakis(ethoxycarbonylethynyl)indates

Youngchul Park, Dongjin Kang, Woo Hyung Jeon, Taekyu Ryu, Phil Ho Lee*

*Department of Chemistry, Kangwon National University, Chuncheon 200-701, Republic of Korea, Email:

Y. Park, D. Kang, W. H. Jeon, T. Ryu, P. H. Lee, Synthesis, 2014, 46, 2305-2311.

DOI: 10.1055/s-0033-1339110 (free Supporting Information)

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A palladium-catalyzed cross-coupling reaction between a wide range of aryl iodides and lithium tetrakis(ethoxycarbonylethynyl)indates (0.35 equiv) enables an efficient synthesis of ethyl arylpropiolates. Lithium tetrakis(ethoxycarbonylethynyl)indates can be generated in situ from ethyl propiolate and n-butyllithium and a subsequent transmetallation with indium trichloride.

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Key Words

cross-coupling, palladium, indium, lithium tetrakis(ethoxycarbonylethynyl)indate, propiolates, catalysis

ID: J66-Y2014