[(acridine)BCl2]+: A Borenium Cation That Is a Strong Boron- and Carbon-Based Lewis Acid

[(acridine)BCl2][AlCl4] was synthesized by halide abstraction from (acridine)BCl3with AlCl3. The hydride ion affinity of the C9 position in [(acridine)BCl2]+was calculated to be 14 kcal mol–1greater than that at boron. [(acridine)BCl2][AlCl4] reacts with 1 equiv of acridine to form the strained boronium cation [(acridine)2BCl2][AlCl4] and with P(mesityl)3by photoinduced one-electron transfer to form the 9,9′-biacridane moiety by radical coupling. A stable frustrated Lewis pair (FLP) was formed on combining [(acridine)BCl2][AlCl4] and 2,4,6-tri-tert-butylpyridine (TBP), which heterolytically activated H2at 100 °C. The ultimate location of the hydride from H2activation was the C9 position of acridine and not boron. Carbon Lewis acid based reactivity also occurred when thieno[3,2-b]thiophene was added to the [(acridine)BCl2][AlCl4]/TBP FLP or to [(acridine)2BCl2][AlCl4], with arylation of acridine at C9 observed for both.