Synthesis of Methylene‐Bridged Bisnaphthalenes as Building Blocks for Push–Pull Substituted Pentacenes

Abstract

The use of cross‐coupling reactions for the synthesis of methylene‐bridged bisnaphthalenes bearing two nitro groups on one naphthalene and two amino groups on the other has been investigated. A Hauser–Heck reaction was used to prepare the substituted naphthalene building blocks. It was not possible to install a transmetallating function in the benzylic position due to side reactions with the nitro and the amino groups. A successful Suzuki reaction was achieved by using naphthyl trifluoroborates and bromomethyl naphthalenes. The resulting dinaphthyl methanes could be useful for the synthesis of push–pull substituted pentacenes.