Preparation and reactions of new zincated nitrogen-containing heterocycles

Article abstract of DOI:10.1016/S0040-4020(97)00427-4

A range of nitrogen-containing iodinated or in some cases brominated heterocycles were converted to the corresponding zincated heterocyclic derivatives by the direct insertion of zinc dust under mild conditions (25°C to 70°C, 1-3 h) in a solvent like THF or DMAC. This reaction was extended to the preparation of zincated nucleic acid bases and nucleosides. The reaction of these new zinc reagents toward various electrophiles with palladium (O) or copper(I) catalysis allows the preparation of a broad range of polyfunctional nitrogen-containing heterocycles.