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Synthesis of Water-Tolerant Indium Homoenolate in Aqueous Media and Its Application in the Synthesis of 1,4-Dicarbonyl Compounds via Palladium-Catalyzed Coupling with Acid Chloride

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posted on 2010-11-17, 00:00 authored by Zhi-Liang Shen, Kelvin Kau Kiat Goh, Hao-Lun Cheong, Colin Hong An Wong, Yin-Chang Lai, Yong-Sheng Yang, Teck-Peng Loh
The first water-tolerant, ketone-type indium homoenolate was synthesized via the oxidative addition of In/InCl3 to enones. The reaction proceeds exclusively in aqueous media. Both indium and indium(III) chloride are necessary for the smooth conversion of the reaction. Similar results were obtained when InCl or InCl2 was used in place of In/InCl3. The synthetic utility of the indium homoenolate was demonstrated through the synthesis of 1,4-dicarbonyl compounds via palladium-catalyzed coupling of indium homoenolate with acid chloride.

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