The 9H-9-Borafluorene Dianion: A Surrogate for Elusive Diarylboryl Anion Nucleophiles.

Double reduction of the THF adduct of 9H-9-borafluorene (1⋅THF) with excess alkali metal affords the dianion salts M2 [1] in essentially quantitative yields (M=Li-K). Even though the added charge is stabilized through π delocalization, [1]2- acts as a formal boron nucleophile toward organoboron (1⋅THF) and tetrel halide electrophiles (MeCl, Et3 SiCl, Me3 SnCl) to form B-B/C/Si/Sn bonds. The substrate dependence of open-shell versus closed-shell pathways has been investigated.