Polymer supported naphthalene-catalysed lithiation reactions

Article abstract of DOI:10.1016/S0040-4039(97)10774-2

The reaction of functionalised mono or dichlorinated materials 1a-6a with an excess of lithium and a catalytic amount of a naphthalene supported polymer (P-152, easily prepared by radical copolymerisation of 2-vinylnaphthalene, styrene and divinylbenzene) in THF either in the presence (Barbier-type conditions) or not of different electrophiles [Me₃SiCl, Bu(n)CHO, Bu(i)CHO, PhCHO, Et₂CO, c(C₃H₅)₂CO, Pr(i)₂CO, (CH₂)₄CO, (CH₂)₅CO, PhCOMe, PhCH=NPh] leads, after hydrolysis, to the expected products 1c-6c. The catalyst is quantitatively recovered and can be reused several times without any loss of its activity.