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The 9 H ‐9‐Borafluorene Dianion: A Surrogate for Elusive Diarylboryl Anion Nucleophiles
Author(s) -
Gilmer Jannik,
Budy Hendrik,
Kaese Thomas,
Bolte Michael,
Lerner HansWolfram,
Wagner Matthias
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201914219
Subject(s) - nucleophile , chemistry , electrophile , halide , alkali metal , boron , medicinal chemistry , delocalized electron , adduct , carbanion , ion , substrate (aquarium) , open shell , umpolung , metal , inorganic chemistry , organic chemistry , catalysis , oceanography , geology
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.