FeCl3 mediated dimerization of dihydropyrrolo[2,1-a]isoquinolines and chlorination of tetrasubstituted pyrroles

We have developed a mild and direct dimerization of dihydropyrrolo[2,1-a]isoquinolines through FeCl3-mediated oxidative homocoupling. A series of dimeric dihydropyrroloisoquinoline derivatives were obtained in acceptable to excellent yields (up to >99%). Attempts to expand this dimerization system to the synthesis of dimeric pyrroles failed and chlorination products were obtained in most cases instead of dimeric pyrroles.