Pd-catalyzed aryl amination mediated by well defined, N-heterocyclic carbene (NHC)-Pd precatalysts, PEPPSI |
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| Authors: | Organ Michael G Abdel-Hadi Mirvat Avola Stephanie Dubovyk Igor Hadei Niloufar Kantchev Eric Assen B O'Brien Christopher J Sayah Mahmoud Valente Cory |
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| Affiliation: | Chemistry Department, York University, 4700 Keele Street, Toronto, M3J 1P3, Canada. organ@yorku.ca |
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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. |
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| Keywords: | amination anilines asymmetric catalysis carbenes palladium |
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