[IPr#-PEPPSI]: A Well-Defined, Highly Hindered and Broadly Applicable Pd(II)-NHC (NHC = N-Heterocyclic Carbene) Precatalyst for Cross-Coupling Reactions

In this Special Issue, Featured Papers in Organometallic Chemistry, we report on the synthesis and characterization of [IPr#-PEPPSI], a new, well-defined, highly hindered Pd(II)-NHC precatalyst for cross-coupling reactions. This catalyst was commercialized in collaboration with MilliporeSigma, Burlington, ON, Canada (no. 925489) to provide academic and industrial researchers with broad access to reaction screening and optimization. The broad activity of [IPr#-PEPPSI] in cross-coupling reactions in a range of bond activations with C-N, C-O, C-Cl, C-Br, C-S and C-H cleavage is presented. A comprehensive evaluation of the steric and electronic properties is provided. Easy access to the [IPr#-PEPPSI] class of precatalysts based on modular pyridine ligands, together with the steric impact of the IPr# peralkylation framework, will facilitate the implementation of well-defined, air- and moisture-stable Pd(II)-NHC precatalysts in chemistry research.

Automated summary

In this Special Issue, a new highly hindered Pd(II)-NHC precatalyst, [IPr#-PEPPSI], was synthesized and characterized for cross-coupling reactions. Commercialized in collaboration with MilliporeSigma, this catalyst provides broad access to reaction screening and optimization for academic and industrial researchers. The broad activity of [IPr#-PEPPSI] in various bond activations and its steric and electronic properties were evaluated, indicating its potential for application in chemistry research.