Application of the Suzuki Reaction as the Key Step in the Synthesis of a Novel Atropisomeric Biphenyl Derivative for Use as a Liquid Crystal Dopant

A heavily functionalized atropisomeric biphenyl derivative (4), which is designed to possess a large lateral dipole moment, has been synthesized with use of a Suzuki coupling as the key step and resolved by chiral HPLC. The final coupling reaction is complicated by rapid hydrolytic deboronation of the sterically hindered, electron poor boronate 22. Rigorously anhydrous conditions are therefore necessary to achieve the coupling.