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DOI: 10.1055/s-2005-861790
The Reduction of Aryl Diethyl Phosphate Esters with Lithium Di-tert-butylbiphenylide Radical Anion: Aromatic Hydrocarbons via the Deoxygenation of Phenols
Publikationsverlauf
Publikationsdatum:
18. Januar 2005 (online)
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Abstract
The reduction of aryl diethyl phosphate esters by lithium 4,4′-di-tert-butylbiphenylide (LiDTBB) in THF at 0 °C is described. The reactions can be carried out either stoichiometrically (3.0 equiv LiDTBB) or with only a catalytic amount of DTBB (0.25 equiv) in the presence of lithium (2.1-3.0 equiv) and the phosphate. Products are separated from DTBB by solubility differences, by acid/base vs. neutral extraction, or by flash chromatography.
Key words
reduction - phosphates - deoxygenation - phenols - arenes
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References
Ar should be used rather than N2 as the inert atmosphere because lithium reacts slowly with nitrogen to form lithium nitride, which coats the lithium surface and can slow the reaction with DTBB.