Arene-catalysed reductive lithiation of tetrahydrofuran: Improved synthesis of 1,5-diols

Article abstract of DOI:10.1016/S0040-4020(01)88496-9

The reductive cleavage of tetrahydrofuran at -78°C can be easily achieved by using an excess of lithium powder in the presence of BF₃-·OEt₂ and a catalytic amount (<8%) of an arene (naphthalene, biphenyl, 4,4'-di-tert-butylbiphenyl or anthracene), the best results being obtained with naphthalene. The dianion prepared by this method reacts with carbonyl compounds yielding 1,5-diols.