TY - JOUR A1 - Kennedy, Sean H. A1 - Gasonoo, Makafui A1 - Klumpp, Douglas A. T1 - Superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups JF - Beilstein Journal of Organic Chemistry PY - 2019/// VL - 15 SP - 1515 EP - 1520 SN - 1860-5397 DO - 10.3762/bjoc.15.153 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.15.153 KW - cation KW - Friedel–Crafts KW - heterocycle KW - superacid KW - superelectrophile N2 - A substrate has been prepared having two triarylmethanol centers and four pyridine-type substituent groups. Upon ionization in the Brønsted superacid CF3SO3H, 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-a]indole rings. With added benzene, an arylation product is obtained. A mechanism is proposed involving tetra-, penta-, or hexacationic species. ER -