title: N-Heterocyclic Carbenes From Laboratories Curiosities to Efficient Synthetic Tools series: RSC Catalysis Series editor: Silvia Díez-González series editor: James J. Spivey publisher: The Royal Society of Chemistry city: Cambridge year: 2010 volume: 6 first page: 196 last page: 227 isbn: 978-1-84973-042-6 doi: 10.1039/9781849732161-00196 |
Abstract: In this chapter, the catalytic applications of organometallic species -either preformed or generated in situ- based on group 8 transition metals and N-heterocyclic carbene (NHC) ligands are surveyed. Thus far, the coordination chemistry of iron with NHCs has not been extensively investigated, and only a few reports on the use of NHC-Fe complexes in organic catalysis are available. They concern mainly polymerisation, cyclisation, and C-C bond forming reactions. Other important examples are found in the related field of biocatalysis and in organometallic synthesis. Contrastingly, the chemistry of NHC-Ru complexes has reached an unprecedented level of maturity, thanks to the relentless research efforts thrown into the development of second and third generation olefin metathesis catalysts. Other carbon skeletal transformations based on NHC-Ru promoters include cyclopropanation, allylation, or cycloisomerisation reactions. Many of these synthetic pathways are used in tandem with a metathetical step. Lastly, with only two reports to date concerning olefin metathesis and transfer hydrogenation, NHC-Os-based catalysis can hardly be considered anything else than a curiosity.