Polymer supported arene-catalysed lithiation reactions

Article abstract of DOI:10.1016/S0040-4020(99)00330-0

The reaction of functionalised mono or dichlorinated materials 1a-6a with an excess of lithium and a catalytic amount of a naphthalene (P(N)) or biphenyl (P(B)) supported polymer (easily prepared by radical copolymerisation of 2-vinylnaphthalene or 4-vinylbiphenyl with vinylbenzene and divinylbenzene) in THF either in the presence or not of different electrophiles [Me₃SiCl, (i)prCHO, PhCHO, Et₂CO, (CH₂)₄CO, (CH₂)₅CO, (c- C₃H₅)₂CO, (i)Pr₂CO, PhCOMe, PhCH=NPh] at -78 or -50°C leads, after hydrolysis with water, to the expected functionalised products 1ca-6ck. The polymeric catalyst is quantitatively recovered and can reused several times without any loss of activity.