Dichloromethane as a source of the CH22-synthon: A combination of an arene-catalysed lithiation and a barbier-type reaction

Article abstract of DOI:10.1016/S0040-4039(00)76524-5

The reaction of dichloromethane 1 with an excess of lithium powder (1:7 molar ratio) and catalytic amount of 4,4'-di-tert-butylbiphenyl (5 mol %) in the presence of a carbonyl compound 2 (1:2 molar ratio) in tetrahydrofuran at -40°C yields, after hydrolysis, the corresponding 1,3-diols 3 in moderate yields. The process can be also applied to more complicated gem-dichloro derivatives such as 7,7-dichlorobicyclo[4.1.0]heptane 6 or methyl dichloromethyl ether 9.