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

Double reduction of the THF adduct of 9 H ‐9‐borafluorene ( 1 ⋅THF) with excess alkali metal affords the dianion salts M 2 [ 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 organo...

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Published in:Angewandte Chemie 2020-03, Vol.132 (14), p.5670-5674
Main Authors: Gilmer, Jannik, Budy, Hendrik, Kaese, Thomas, Bolte, Michael, Lerner, Hans‐Wolfram, Wagner, Matthias
Format: Article
Language:English
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Summary:Double reduction of the THF adduct of 9 H ‐9‐borafluorene ( 1 ⋅THF) with excess alkali metal affords the dianion salts M 2 [ 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, Et 3 SiCl, Me 3 SnCl) to form B−B/C/Si/Sn bonds. The substrate dependence of open‐shell versus closed‐shell pathways has been investigated.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201914219