Multicomponent Synthesis of Unsymmetrical Unsaturated N-Heterocyclic Carbene Precursors and Their Related Transition-Metal Complexes

• Published in: Angewandte Chemie (International ed.) Vol. 52; no. 52; pp. 14103 - 14107
• Main Authors: Queval, Pierre, Jahier, Claire, Rouen, Mathieu, Artur, Isabelle, Legeay, Jean-Christophe, Falivene, Laura, Toupet, Loic, Crévisy, Christophe, Cavallo, Luigi, Baslé, Olivier, Mauduit, Marc
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 23.12.2013; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc; Wiley-VCH Verlag
• Edition: International ed. in English
• Subjects: Carbenes; Chemical bonds; Chemical Sciences; Chemistry; Chemistry, Multidisciplinary; chirality; Demand; Discrimination; Electronics; ligand design; Ligands; Modular; multicomponent reactions; N-heterocyclic carbenes; Other; Physical Sciences; R&D; Research & development; Science & Technology; Selectivity; transition metals; Unsaturated; multicomponent reactions; chirality; LIGANDS; transition metals; ligand design; ALKYL AMINO CARBENES; RESTRICTED FLEXIBILITY; METATHESIS; CATALYSTS; N-heterocyclic carbenes; transition metal complex cycloalkyl imidazolidene carbene prepn crystal structure; aryl cycloalkyl imidazolium salt prepn crystal mol structure reaction; unsym unsatd heterocyclic imidazolidene carbene precursor multicomponent synthesis
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201308873

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. A low‐cost, modular, and easily scalable multicomponent procedure, affording access to a wide range of (a)chiral unsymmetrical 1‐aryl‐3‐cycloalkyl‐imidazolium salts in good yields and excellent selectivities, 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.