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