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Pd-Catalyzed Aryl Amination Mediated by Well Defined, N-Heterocyclic Carbene (NHC)–Pd Precatalysts, PEPPSI

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

Publisher: John Wiley and Sons
Year: 2008
Tongue: English
Weight: 395 KB
Volume: 14
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.200701621

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✦ Synopsis

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 (p__K__~b~) requirements is also provided.

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