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N-Heterocyclic Carbene Complexes in Dehalogenation Reactions

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N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis

Part of the book series: Catalysis by Metal Complexes ((CMCO,volume 32))

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Abstract

Catalytic dehalogenation represents an underdeveloped transformation in M–NHC chemistry with a small number of reports detailing the reactivity of Co, Ru, Ni and Pd catalysts. In situ generated nickel and palladium NHC complexes catalyse the hydrodechlorination of aryl chlorides. Lower coordinate Ni complexes are proposed to operate in the hydrodefluorination of mono- and poly-fluorinated substrates. The single example of Ru–NHC catalysed hydrodefluorination of fully and partially fluorinated aromatic substrates is characterised by an unusual regioselectivity. The highly regioselective dehydrohalogenation of relatively unreactive alkyl halide substrates is achieved with a cobalt NHC catalyst.

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Acknowledgements

The authors would like to thank the Spanish Ministerio de Ciencia e Innovación (EMM) and the EPSRC (MJP) for financial support.

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Correspondence to Michael K. Whittlesey .

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Mas-Marzá, E., Page, M.J., Whittlesey, M.K. (2010). N-Heterocyclic Carbene Complexes in Dehalogenation Reactions. In: Cazin, C. (eds) N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis. Catalysis by Metal Complexes, vol 32. Springer, Dordrecht. https://doi.org/10.1007/978-90-481-2866-2_8

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