Boryllithium: isolation, characterization, and reactivity as a boryl anion - PubMed
- ️Sun Jan 01 2006
. 2006 Oct 6;314(5796):113-5.
doi: 10.1126/science.1131914.
Affiliations
- PMID: 17023656
- DOI: 10.1126/science.1131914
Boryllithium: isolation, characterization, and reactivity as a boryl anion
Yasutomo Segawa et al. Science. 2006.
Erratum in
- Science. 2006 Dec 15;314(5806):1683
Abstract
Nucleophilic, anionic boryl compounds are long-sought but elusive species. We report that reductive cleavage of the boron-bromine bond in N,N'-bis(2,6-diisopropylphenyl)-2-bromo-2,3-dihydro-1H-1,3,2-diazaborole by lithium naphthalenide afforded the corresponding boryllithium, which is isoelectronic with an N-heterocyclic carbene. The structure of the boryllithium determined by x-ray crystallography was consistent with sp(2) boron hybridization and revealed a boron-lithium bond length of 2.291 +/- 0.006 angstroms. The structural similarity between this compound and the calculated free boryl anion suggests that the boron atom has an anionic charge. The (11)B nuclear magnetic resonance spectrum also supports the boryl anion character. Moreover, the compound behaves as an efficient base and nucleophile in its reactions with electrophiles such as water, methyl trifluoromethanesulfonate, 1-chlorobutane, and benzaldehyde.
Comment in
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Chemistry. Boron goes on the attack.
Marder TB. Marder TB. Science. 2006 Oct 6;314(5796):69-70. doi: 10.1126/science.1133326. Science. 2006. PMID: 17023642 No abstract available.
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