Synthesis of stilbene, 1,4-distyrylbenzene and 4,4′-distyrylbiphenyl via Horner–Wadsworth–Emmons reaction in phase-transfer catalysis system

Abstract

Stilbenes, 1,4-distyrylbenzenes and 4,4′-distyrylbiphenyls were synthesized via Horner–Wadsworth–Emmons (HWE) reaction in liquid–liquid (LL) and solid–liquid (SL) phase transfer catalysis (PTC) systems. The effect of the side reaction, reactants and the third phase on the activity of HWE reaction were investigated. For aldehydes bearing electron-donating substitute, the yields were more than 90% and the products were all (E)-isomers in both PTC systems. The SL-PTC system was milder than LL-PTC system for HWE reaction due to the different mechanisms. The side reaction of aldehyde was similar to Cannizzaro reaction, whereas the molar ratio of benzoic acid to benzyl alcohol as the products was not 1:1. The limited third phase was discovered to exist in LL-PTC system. In SL-PTC system, the third phase could increase substantially the reaction rate. Moreover, the aqueous phase in LL-PTC system could be reused four times without sacrifice of the yield and reaction rate.