A substrate has been prepared having two triarylmethanol centers and four pyridine-type substituent groups. Upon ionization in the Brønsted superacid CFSOH, the substrate undergoes two types of reactions. In the presence of only the superacid, the highly ionized intermediate(s) provide a double cyclization product having two pyrido[1,2-]indole rings. With added benzene, an arylation product is obtained. A mechanism is proposed involving tetra-, penta-, or hexacationic species.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6633208PMC
http://dx.doi.org/10.3762/bjoc.15.153DOI Listing

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