1033752-75-8Relevant academic research and scientific papers
Amination with Pd-NHC complexes: Rate and computational studies on the effects of the oxidative addition partner
Hoi, Ka Hou,Calimsiz, Selcuk,Froese, Robert D. J.,Hopkinson, Alan C.,Organ, Michael G.
supporting information; experimental part, p. 3086 - 3090 (2011/04/25)
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.
Pd-catalyzed aryl amination mediated by well defined, N-heterocyclic carbene (NHC)-Pd precatalysts, PEPPSI
Organ, Michael G.,Abdel-Hadi, Mirvat,Avola, Stephanie,Dubovyk, Igor,Hadei, Niloufar,Kantchev, Eric Assen B.,O'Brien, Christopher J.,Sayah, Mahmoud,Valente, Cory
experimental part, p. 2443 - 2452 (2009/04/08)
Pd-N-heterocyclic carbene (NHC)-catalyzed Buchwald-Hartwig animation protocols mediated by Pd-PEPPSI precatalysts is described. These protocols provide access to a range of hindered and functionalized drug-like aryl amines in high yield with both electron-deficient and electron-rich aryl- and heteroaryl chlorides and bromides. Variations in solvent polarity, base and temperature are tolerated, enhancing the scope and utility of this protocol. A mechanistic rationalization for base strength (pKb) requirements is also provided.
