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 LernerORCiDGND, Matthias WagnerORCiD |
|---|---|
| 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 |
