Research output: Contribution to journal › Article › peer-review
Journal | Organometallics |
---|---|
Date | Published - 27 Jul 2015 |
Issue number | 14 |
Volume | 34 |
Number of pages | 11 |
Pages (from-to) | 3497-3507 |
Original language | English |
Cu<sup>I</sup>(NHC)Br complexes (NHC = N-heterocyclic carbene) undergo a direct reaction with iodobenzene to give 2-arylated benzimidazolium products. The nature of the N-substituent on the NHC ligand influences the reactivity of the Cu<sup>I</sup>(NHC)Br complex toward arylation. N-Benzyl or N-phenyl substituents facilitate arylation, whereas N-mesityl substituents hinder arylation. Density functional theory calculations show that an oxidative addition/reductive elimination pathway involving Cu<sup>III</sup> species is energetically feasible. A less hindered Cu<sup>I</sup>(NHC)Br complex with N-benzyl groups is susceptible to oxidation reactions to give 1,3-dibenzylbenzimidazolium cations containing a Cu<sup>I</sup>Br anion (various polymorphs). The results described herein are of relevance to C-H functionalization of (benz)azoles. (Chemical Equation Presented).
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