The synthesis of novel highly substituted benzene derivatives for use in palladium-catalysed cross-coupling reactions

Abstract

A combination of conventional electrophilic aromatic substitution reactions and low-temperature ortho-directed lithiations has been used in the efficient synthesis of some novel highly substituted benzene derivatives containing alkoxy, alkyl, bromo, cyano, fluoro and iodo functions. The use of such compounds is exemplified by selective palladium-catalysed cross-coupling reactions to generate a series of liquid crystalline terphenyls with a lateral fluoro substituent ortho to a lateral cyano group.