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.
Author: | Jannik Gilmer, Hendrik Budy, Thomas Kaese, Michael BolteORCiD, Hans-Wolfram LernerORCiDGND, Matthias WagnerORCiD |
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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): | Creative Commons - Namensnennung-Nicht kommerziell - Keine Bearbeitung 4.0 |