Palladium-catalysed cross-coupling reactions in the synthesis of some high polarizability materials

Liquid crystal materials of high optical anisotropy consist of moieties of high electron density in conjugation with each other along the molecular length. Such structures are conducive to convergent synthesis methods. Here we report the synthesis of a range of novel materials by the strategic use of palladium-catalysed cross-coupling methods. In addition to the traditional use of bromide and iodide leaving groups, invaluable use of the triflate leaving group and the importance of selective cross-coupling methods using both arylboronic acids and alkynylzinc chloride derivatives is illustrated. This systematic methodology allows the separate synthesis of the appropriate sub-units that can be efficiently coupled together to provide high overall product yields.