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

Zhi-Liang Shen; Kelvin Kau Kiat Goh; Hao-Lun Cheong; Colin Hong An Wong; Yin-Chang Lai; Yong-Sheng Yang; Teck-Peng Loh

doi:10.1021/ja106925f

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

J Am Chem Soc. 2010 Nov 17;132(45):15852-5. doi: 10.1021/ja106925f. Epub 2010 Oct 21.

Authors

Zhi-Liang Shen¹, Kelvin Kau Kiat Goh, Hao-Lun Cheong, Colin Hong An Wong, Yin-Chang Lai, Yong-Sheng Yang, Teck-Peng Loh

Affiliation

¹ Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.

PMID: 20964387
DOI: 10.1021/ja106925f

Abstract

The first water-tolerant, ketone-type indium homoenolate was synthesized via the oxidative addition of In/InCl(3) 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 InCl(2) was used in place of In/InCl(3). 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.