Iteroselectivity, the missing sibling of chemo-, regio- and stereoselectivities

Abstract

Iteroselectivity is the selectivity that governs the number of repeating chemical transformations on a substrate bearing multiple identical reactive functions or when the reactive function is regenerated like in the case of polymerization. This new concept of selectivity is defined and compared with the classical chemo-, regio- and stereoselectivities encountered in chemical synthesis. Examples of iteroselective reactions are given ranging from very common reactions such as electrophilic aromatic substitutions to advanced methods involving large supramolecular complexes.