Synthesis and Reduction of a Cyclic (Alkyl)(amino)bromoborane to Generate a Thermally Labile Cyclic (Alkyl)(amino)boryl Anion

Synthesis and Reduction of a Cyclic (Alkyl)(amino)bromoborane to Generate a Thermally Labile Cyclic (Alkyl)(amino)boryl Anion

A cyclic (alkyl)(amino)bromoborane (CAABBr) was synthesized by a reaction of the corresponding hydroborane with bromine in the presence of triethylamine. Reduction of the resulting CAABBr with Li powder and 4,4′-di-tert-butylbiphenyl (DBB) generated a thermally labile cyclic (alkyl)(amino)boryllithi...

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Veröffentlicht in:Chemistry letters 2021-02, Vol.50 (2), p.293-296
Hauptverfasser: Kisu, Haruki, Kosai, Tomoyuki, Iwamoto, Takeaki, Yamashita, Makoto
Format: Artikel
Sprache:eng
Schlagworte:
Bromine
Chemical synthesis
Low temperature
NMR spectroscopy
Reduction
Triethylamine
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Zusammenfassung:A cyclic (alkyl)(amino)bromoborane (CAABBr) was synthesized by a reaction of the corresponding hydroborane with bromine in the presence of triethylamine. Reduction of the resulting CAABBr with Li powder and 4,4′-di-tert-butylbiphenyl (DBB) generated a thermally labile cyclic (alkyl)(amino)boryllithium (CAABLi) which was characterized by NMR spectroscopy. Quenching of the mixture reduced by Li/DBB with methanol-d1 or MeOTf at low temperature gave a deuterioborane or methylborane, supporting the generation of CAABLi.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.200749