Amination with Pd-NHC complexes: rate and computational studies on the effects of the oxidative addition partner |
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Authors: | Hoi Ka Hou Çalimsiz Selçuk Froese Robert D J Hopkinson Alan C Organ Michael G |
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Institution: | Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3, Canada. |
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Abstract: | Pd-PEPPSI-IPent, a recently-developed N-heterocyclic carbene (NHC) complex, has been evaluated in amination reactions with secondary amines and it has shown superb reactivity under the most mildly basic reaction conditions. Rate and computational studies were conducted to provide insight into the mechanism of the transformation. The IPent catalyst coordinates to the amine much more strongly than the IPr variant, thus favouring deprotonation with comparatively weak bases. Indeed the reaction is first order in base and only slightly more than zeroth order in amine. |
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Keywords: | amination carbene ligands catalysis computational chemistry kinetics palladium |
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