Understanding the regioselectivity in Scholl reactions for the synthesis of oligoarenesElectronic supplementary information (ESI) available. See DOI: 10.1039/c1cc15980a

A short reaction sequence leads to oligoarene derivatives utilising a regioselective Scholl reaction for the unprecedented cyclisation to the mono-functionalised oligoarene under methanol elimination. Quantum-chemical investigations reveal the reason for the remarkably high regioselectivity. A regioselective Scholl reaction for the unprecedented cyclisation to the mono-functionalised oligoarene is reported and its formation rationalised by quantum-chemical investigations.