Lithiated benzyllithiums from chlorobenzyl chlorides by a DTBB-catalysed lithiation

Article abstract of DOI:10.1016/S0040-4039(96)02393-3

The reaction of 2-, 3- or 4-chlorobenzyl chlorides (1a-c) with an excess of lithium and a catalytic amount of DTBB (7 mol%) in the presence of different electrophiles [Pr(i)CHO, Bu(t)CHO, Et₂CO, (CH₂)₅CO, PhCOMe, Me₃SiCl] in THF at -50°C leads after hydrolysis with water, to the expected dioles or disilylated compounds 2aa-2cf.