Organolead(iv) triacetates in organic synthesis

Abstract

Organolead triacetates have been developed as relatively cheap and versatile reagents for the electrophilic arylation, vinylation and alkynylation of soft carbon nucleophiles. Their reactions with phenols and β-dicarbonyls, in particular, illustrate their unique regioselectivity in which they display a marked preference for the generation of quaternary cabon centres. This aspect of their reactivity has been put to use in a number of natural product syntheses and can result in the formation of highly hindered structures. The main features of these reactions and their mechanisms, which are shown to involve ligand coupling, are discussed.