Preparation of 2,3,3-Triarylacrylic Acid Esters Using Suzuki–Miyaura Coupling Reactions

Abstract

We report here a new strategy to produce 2,3,3-triarylacrylic acid esters, a class of 1,2,2-triarylethene compounds with an α,β-unsaturated ester functionality. Our approach requires the preparation of a gem-dibromoalkene precursor from an α-keto ester, followed by the installation of two aryl groups by Suzuki–Miyaura coupling reactions on the two C–Br bonds. Many 2,3,3-triarylacrylic acid esters with one, two, or three different aryl groups were obtained with complete regio- and stereocontrol in most cases.

Key words

triarylethene - triarylacrylic acid - gem-dibromoalkene - double Suzuki–Miyaura coupling - stereoselective Suzuki–Miyaura coupling

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