An efficient method for the synthesis of ester-containing indium homoenolate via a direct insertion of indium into β-halo ester in the presence of CuI/LiCl was described. The synthetic utility of the indium homoenolate was demonstrated by palladium-catalyzed cross-coupling with aryl halides in DMA with wide functional group compatibility.
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http://dx.doi.org/10.1039/c0cc05597b | DOI Listing |
Chem Commun (Camb)
April 2011
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.
An efficient method for the synthesis of ester-containing indium homoenolate via a direct insertion of indium into β-halo ester in the presence of CuI/LiCl was described. The synthetic utility of the indium homoenolate was demonstrated by palladium-catalyzed cross-coupling with aryl halides in DMA with wide functional group compatibility.
View Article and Find Full Text PDFOrg Lett
February 2011
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.
An efficient palladium-catalyzed cross-coupling of indium homoenolate with aryl halide is described. The reactions proceeded efficiently in DMA at 100 °C to afford the desired products of β-aryl ketones in moderate to good yields. Various important functional groups including COR, COOR, CHO, CN, OH, and NO(2) can be well tolerated in the protocol.
View Article and Find Full Text PDFJ Am Chem Soc
November 2010
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.
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.
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