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

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Abstract

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, Et3SiCl, Me3SnCl) 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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Gilmer, J., Budy, H., Kaese, T., Bolte, M., Lerner, H. W., & Wagner, M. (2020). The 9H-9-Borafluorene Dianion: A Surrogate for Elusive Diarylboryl Anion Nucleophiles. Angewandte Chemie - International Edition, 59(14), 5621–5625. https://doi.org/10.1002/anie.201914219

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