Diethylzinc Amylates: Selective Iodine-Zinc Exchange Reagents at Room Temperature

Abstract

The cheapest available organozinc species (diethylzinc), yet rarely employed in halogen-Zn exchange, is used in a combination with amylate salts to generate new, over time, stable reagents that allow smooth iodide-zinc exchange at room temperature, preventing therefore the need for the fastidious and time-consuming preparation of complex mixtures. The scope of the reaction has been explored on polyfunctionalized alkenes (including sensitive cyclobutenes, steroids, and glycals), aryls, and heteroaryls.