NDLI: Alcohol-Induced C−N Bond Cleavage of Cyclometalated N-Heterocyclic Carbene Ligands with a Methylene-Linked Pendant Imidazolium Ring

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Alcohol-Induced C−N Bond Cleavage of Cyclometalated N-Heterocyclic Carbene Ligands with a Methylene-Linked Pendant Imidazolium Ring

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Zhong, Wei Fei, Zhaofu Dyson, Paul J. Scopelliti, Rosario
Description	Author Affiliation: Zhong W ( Institut des Sciences et Ingénierie Chimiques, Ecole Polytechnique Fédérale de Lausanne (EPFL), 1015, Lausanne, Switzerland.); Fei Z ( College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, 314001, China.); Scopelliti R ( Institut des Sciences et Ingénierie Chimiques, Ecole Polytechnique Fédérale de Lausanne (EPFL), 1015, Lausanne, Switzerland.); Dyson PJ ( Institut des Sciences et Ingénierie Chimiques, Ecole Polytechnique Fédérale de Lausanne (EPFL), 1015, Lausanne, Switzerland.)
Abstract	Reaction of the pentamethylcyclopentadienyl rhodium iodide dimer $[CpRhI_{2}]_{2}$ with 1,1′-diphenyl-3,3′-methylenediimidazolium diiodide in non-alcohol solvents, in the presence of base, led to the formation of bis-carbene complex [CpRh(bis-NHC)I]I (bis-NHC=1,1′-diphenyl-4,4′-methylenediimidazoline-5,5′-diylidene). In contrast, when employing alcohols as the solvent in the same reaction, cleavage of a methylene C−N bond is observed, affording ether-functionalized (cyclometalated) carbene ligands coordinated to the metal center and the concomitant formation of complexes with a coordinated imidazole ligand. Studies employing other 1,1′-diimidazolium salts indicate that the cyclometalation step is a prerequisite for the activation/scission of the C−N bond and, based on additional experimental data, a $S_{N}2$ mechanism for the reaction is tentatively proposed.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	34
Volume Number	22
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2016-08-16
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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