The use of McMurry coupling for the synthesis of indolophanes and cis-stilbenophanes

Treatment of 2 equiv of indole-3-aldehyde with o, m, p-xylyl, 2,5-dimethoxy-p-xylyl dibromides and 4,4′-bis(bromomethyl)-1,1′-biphenyl gave the bisalkylated products, which underwent McMurry coupling with low valent titanium to give indolophanes. Various cis-stilbenophanes with m-terphenyl building blocks were also synthesized by application of the McMurry coupling technique.