Multicomponent synthesis of unsymmetrical unsaturated N-heterocyclic carbene precursors and their related transition-metal complexes

Angew Chem Int Ed Engl. 2013 Dec 23;52(52):14103-7. doi: 10.1002/anie.201308873. Epub 2013 Dec 4.

Abstract

A low-cost, modular, and easily scalable multicomponent procedure affording access in good yields and excellent selectivity (up to 93%) to a wide range of (a)chiral unsymmetrical 1-aryl-3-cycloalkyl-imidazolium salts is disclosed. Electronic and steric properties of the corresponding unsymmetrical unsaturated N-heterocyclic carbene (U2-NHC) ligands were evaluated and evidenced strong electron donor ability, high steric discrimination, and modular steric demand.

Keywords: N-heterocyclic carbenes; chirality; ligand design; multicomponent reactions; transition metals.