Nucleophilic ipso-Substitution of Aryl Methyl Ethers through Aryl C-OMe Bond Cleavage; Access to Functionalized Bisthiophenes.

A metal and solvent free strategy to functionalize aryl methyl ethers through direct nucleophilic substitution of aryl C-OMe bond has been described. A wide range of O, S, N, and C-centered uncharged nucleophiles has been successfully employed. Using this protocol, functional derivatives of bisthiophene have been synthesized in a straightforward way. The reactions are highly atom-efficient and generate methanol as the only byproduct.