Issue 28, 2016

Theoretical rationalisation for the mechanism of N-heterocyclic carbene-halide reductive elimination at CuIII, AgIII and AuIII

Abstract

Reductive elimination of imidazolium salts from CuIII is extremely sensitive to the anionic ligand (X or Y) type on Cu (e.g. ΔG ranges from 4.7 kcal mol−1 to 31.8 kcal mol−1, from chloride to benzyl). Weakly σ-donating ligands dramatically accelerate reductive elimination. Comparison with Ag/Au shows that the HOMO energy, strength of M–NHC and M–Y bonds and inherent stability of MIII with respect to MI are critical to governing reaction feasibility.

Graphical abstract: Theoretical rationalisation for the mechanism of N-heterocyclic carbene-halide reductive elimination at CuIII, AgIII and AuIII

Supplementary files

Article information

Article type
Communication
Submitted
11 Feb 2016
Accepted
02 Mär 2016
First published
18 Mär 2016

Chem. Commun., 2016,52, 5057-5060

Author version available

Theoretical rationalisation for the mechanism of N-heterocyclic carbene-halide reductive elimination at CuIII, AgIII and AuIII

Y. Younesi, B. Nasiri, R. BabaAhmadi, C. E. Willans, I. J. S. Fairlamb and A. Ariafard, Chem. Commun., 2016, 52, 5057 DOI: 10.1039/C6CC01299J

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