N-Heterocyclic Carbenes in Transition Metal Catalysis by Frank Glorius

By Frank Glorius

In this e-book top specialists have surveyed significant components of program of NHC steel complexes in catalysis. The authors have put a distinct specialize in nickel- and palladium-catalyzed reactions, on purposes in metathesis reactions, on oxidation reactions and at the use of chiral NHC-based catalysts. This compilation is rounded out by way of an introductory bankruptcy and a bankruptcy facing man made routes to NHC steel complexes.

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Miscellaneous Cross-coupling Reactions . . . . . . . . . . . . . . . 52 52 53 53 54 57 58 59 59 60 61 63 63 64 65 5 Dehalogenation Reactions . . . . . . . . . . . . . . 3 Transformations Through C–H Activation Oxidation of Methane to Methanol . . Direct Arylation Reactions . . . . . Hydroarylation of Alkynes . . . . . . . 66 66 67 68 7 Cyclization of Enynes . . . . . . . . . . . . . . . 69 8 Hydrogenation Reactions . . . . . . .

A somewhat different result is obtained from analogous reactions with the NHC-coordinated complex, (IMes)2 Pd0 (11a). This complex is extremely air-sensitive and reacts with dioxygen, even in the solid state, to produce the peroxo-complex, (IMes)2 Pd(η2 -O2 ) (12a). Addition of acetic acid to this complex yields the hydroperoxide complex, trans-(IMes)2 Pd(OAc)(OOH) (13). Prolonged reactions times are necessary before the second equivalent of acetic acid reacts to produce hydrogen peroxide and (IMes)2 Pd(OAc)2 (14) [44] (Scheme 2).

43 References . . . . . . . . . . . . . . . . . . . . 43 Complexes . . . . . . . . . . . . . . . . . . . . . . . . . Abstract N-Heterocyclic carbenes (NHCs) possess properties that are ideally suited for their use as ligands in transition-metal oxidation chemistry and catalysis. Their strong sigma-donating ability stabilizes metals in high oxidation states, and their high M–L bond dissociation energies reduce their tendency to dissociate and undergo oxidative decomposition of the free carbene.

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