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Bifunctional organometallic catalysts offer unique opportunities for new and improved reactivity and selectivity. The combination of a metal's d electrons and a pendant base or acid in the vicinity of an organometallic active site leads to substantial improvement of reaction rate in many key reactions. Here we report a synthesis of the first example of an imidazol-2-yl substituted bifunctional N-heterocyclic carbene ligand (NHC) and its coordination to a variety of metals. The metal complexes have been characterized by IR, NMR, and X-ray crystallography. The catalytic activity of these new NHC-metal complexes in hydrogenation reactions (e.g. Oppenauer-type alcohol oxidation, ß-alkylation of secondary alcohols with primary alcohols, N-alkylation of amines with alcohols), hydroamination, and azide-alkyne cycloaddition reactions is described.
In this book leading experts have surveyed major areas of application of NHC metal complexes in catalysis. The authors have placed a special focus on nickel- and palladium-catalyzed reactions, on applications in metathesis reactions, on oxidation reactions and on the use of chiral NHC-based catalysts. This compilation is rounded out by an introductory chapter and a chapter dealing with synthetic routes to NHC metal complexes.
This book meets the long-felt need for a reference on ferrocenes with the focus on catalysis. It provides a thorough overview of the synthesis and characterization of different types of chiral ferrocene ligands, their application to various catalytic asymmetric reactions, and versatile chiral materials as well as drug intermediates synthesized from them. Written by the "who's who" of ferrocene catalysis, this is a guide to the design of new ferrocene ligands and synthesis of chiral synthetic intermediates, and will thus be useful for organic, catalytic and synthetic chemists working in academia, industrial research or process development.
The use of N-heterocyclic carbenes (NHCs) as ligands in catalysis is one of the most significant developments in modern catalysis and organometallic chemistry. One way to extend the scope of NHC ligand tuning is by means of annulation of carbocyclic and heterocyclic rings to the NHC backbone. The bis(imino)acenaphthene-supported N-heterocyclic carbene [IPr(BIAN)] has been synthesized and can be regarded as originating from the fusion of a naphthalene ring to an NHC. Several metal complexes of IPr(BIAN), including those incorporating copper(I), silver(I), gold(I), or iridium(I) have been synthesized and characterized, including single-crystal X-ray diffraction studies. The doncity of IPr(BIAN) was investigated using the Tolmen Electronic Parameter (TEP) method. A TEP value of 2042 cm−1 was calculated for the IPr(BIAN) ligand using the Ir(CO)2Cl complex which indicates that IPr(BIAN) is a relatively strong electron donating NHC ligand. The well-behaved redox chemistry of the BIAN ligand class rendered IPr(BIAN) an excellent candidate for exploration of the relationship between ligand charge and carbene donicity. The electrochemical reduction of IPr(BIAN) was studied by cyclic voltammetry (CV) in a THF solution and a reversible reduction wave was detected at - 1.79 V vs SCE. Spectroelectrochemical IR studies were also undertaken to further characterize the nature of the reduced state. IPr(BIAN) was found to be a stronger electron donating ligand in the reduced state in comparison with the neutral state of the ligand. IPr(BIAN) was also chemically reduced using potassium graphite and the resulting radical anion was studied by electron paramagnetic resonance (EPR) techniques. An isotropic EPR signal was observed at a g value of 2.0112. Due to the known antimicrobial activities of silver and gold NHCs, the activities of the silver and gold complexes of IPr(BIAN) and the imidazolium salts of several BIAN ligands were investigated using the minimum inhibitory concentration test. The silver(I) and gold(I) complexes of IPr(BIAN) were found to be moderately active. The most active compounds were found to be the imidazolium salts, with MIC values ranging between
Summarizing the emerging field of N-heterocyclic carbenes used in organocatalysis, this is an excellent overview of the synthesis and applications of NHCs focusing on carbon-carbon and carbon-heteroatom bond formation. Alongside comprehensive coverage of the synthesis, characteristics and applications, this handbook and ready reference also includes chapters on NHCs for polymerization reactions and natural product synthesis.