Pd-catalyzed aryl amination mediated by well defined, N-heterocyclic carbene (NHC)-Pd precatalysts, PEPPSI.

Michael G Organ, Mirvat Abdel-Hadi, Stephanie Avola, Igor Dubovyk, Niloufar Hadei, Eric Assen B Kantchev, Christopher J O'Brien, Mahmoud Sayah, Cory Valente

Index: Chemistry 14 , 2443, (2008)

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Abstract

Pd-N-heterocyclic carbene (NHC)-catalyzed Buchwald-Hartwig amination 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.