CAS 141556-42-5 1,3-Dimesitylimidazol-2-ylidene

Synonyms

IMes; 1,3-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene;1,3-Bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene ;

Molecular Weight

304.43

Molecular Formula

C21H24N2

Melting Point

155°C

Purity

97%

Storage

Protect from light, store at -20°C, fill with argon

Application

The purpose of 1,3-Dimesitylimidazol-2-ylidene is to act as a nucleophilic N-heterocyclic carbene (NHC) ligand in various catalytic processes. It is utilized to create complexes such as the IMes ligated-rhodium catalyst, which is effective for the selective hydrogenation of substituted aryl and heteroaryl boronate esters into cis-substituted borylated cycloalkanes. Additionally, its role is significant in forming the IMes/ruthenium complex (Cp*Ru(IMes)Cl) used as a catalyst in olefin ring-closing metathesis reactions. As an ancillary ligand, it also plays a vital part in palladium-catalyzed Suzuki-Miyaura cross-coupling reactions involving aryl chlorides or aryl triflates with arylboronic acids. Acting as a bulky, electron-rich "phosphine mimic," 1,3-Dimesitylimidazol-2-ylidene enhances metal-catalyzed reactions, including palladium-catalyzed Suzuki cross-coupling of aryl chlorides and enhancing the reactivity of ruthenium-carbene complexes in ring-closing metathesis.

February 8, 2025

Excellent Ligand for Catalysis

I used Alfa Chemistry's 1,3-Dimesitylimidazol-2-ylidene in my lab for rhodium-catalyzed hydrogenation. Its role as a robust NHC ligand greatly enhanced the efficiency of our reactions, particularly in Suzuki-Miyaura couplings.