Arylation of Enolate Equivalents

Aryllead, vinyllead, and alk-l-ynyllead tricarboxylates behave as aryl, vinyl and alkynyl cation equivalents to react with a variety of nucleophiles, especially soft carbon nucleophiles such as T -dicarbonyl compounds, phenols, and nitroalkanes. In these reactions, unique regioselectivity is obtained in which there is a preference for the generation of quaternary carbon centers. This aspect of reactivity has been put to use in a number of natural product syntheses and can result in the formation of highly hindered structures. 

Syntheses of the anti-inflammatory compound 2-(p-isobutylphenyl)propanoic 

---

Conditions for arylation of enolate equivalents have also been developed. In the presence of ZnF2, silyl enol ethers, silyl ketene acetals, and similar compounds react. For example, the TMS derivatives of /V-acyl oxazolidinones can be arylated. 

---