Synthesis of novel α-acyloxycarboxamides containing vinylbis(silanes) through three-component Passerini reactions

Abstract

A three-component efficient procedure is described for the synthesis of novel α-acyloxycarboxamides containing bis(trimethylsilyl)ethenyl group from 4-[2,2-bis(trimethylsilyl)ethenyl]benzaldehyde, aromatic carboxylic acids and isocyanides, via the Passerini reaction. This reaction proceeds smoothly and cleanly under mild conditions in H2O and [bmim]BF4 at room temperature and led to products in good yields. The silylated aldehyde was obtained via Peterson olefination reaction of terephthalaldehyde with tris(trimethylsilyl)methyllithium in THF at 0 °C.