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 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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Author:Jannik Gilmer, Hendrik Budy, Thomas Kaese, Michael BolteORCiD, Hans-Wolfram LernerGND, Matthias Wagner
URN:urn:nbn:de:hebis:30:3-638237
DOI:https://doi.org/10.1002/anie.201914219
ISSN:1521-3773
Parent Title (English):Angewandte Chemie
Publisher:Wiley-VCH
Place of publication:Weinheim
Document Type:Article
Language:English
Date of Publication (online):2019/12/13
Date of first Publication:2019/12/13
Publishing Institution:Universitätsbibliothek Johann Christian Senckenberg
Release Date:2022/03/08
Tag:boron; boryl anions; nucleophilic substitution; radical reactions; umpolung
Volume:59
Issue:14
Page Number:5
First Page:5621
Last Page:5625
HeBIS-PPN:493367985
Institutes:Biochemie, Chemie und Pharmazie
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Sammlungen:Universitätspublikationen
Licence (German):License LogoCreative Commons - Namensnennung-Nicht kommerziell - Keine Bearbeitung 4.0