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 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 (...

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Detalles Bibliográficos
Autores principales: Gilmer, Jannik, Budy, Hendrik, Kaese, Thomas, Bolte, Michael, Lerner, Hans‐Wolfram, Wagner, Matthias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7155136/
https://www.ncbi.nlm.nih.gov/pubmed/31834978
http://dx.doi.org/10.1002/anie.201914219
Descripción
Sumario:Double reduction of the THF adduct of 9H‐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.

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