Electron-Accepting Dithiarubicene (Emeraldicene) and Derivatives Prepared by Unprecedented Nucleophilic Hydrogen Substitution by Alkyllithium Reagents

By understanding the role of DMF as a hydride source via a Pd-catalyzed reaction and switching to CH(3)CN solvent, an efficient route for the synthesis of emeraldicene and some new substituted derivatives is reported with potential application in organic electronics. Additionally, the nucleophilic alkylation of emeraldicene 4a with alkyllithium reagents provides monosubstituted compounds 7a and 7b, the latter crystallizing in columnar stacks, with pi-pi overlap between adjacent molecules in the stack.