The influential IPr: 25 years after its discovery.

Abstract

N-Heterocyclic carbenes (NHCs) have emerged as a privileged ligand family in organometallic chemistry, widely recognized for their unique steric and electronic properties. Among them, the 1,3-bis(2,6-diisopropylphenyl)imidazole-2-ylidene (IPr) ligand has become a cornerstone of NHC chemistry for its remarkable versatility, stability, and broad use. Since its discovery by the Nolan group in 1999, IPr has played a pivotal role in advancing catalytic transformations and facilitating the utilization of NHC ligands in various domains. This article highlights major contributions where IPr has helped shape modern organometallic chemistry, with a focus on its influence in transition metal catalysis and ligand design. Twenty five years after its discovery, the IPr ligand continues to be a benchmark ligand, inspiring and driving innovation.