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Pd‐Catalyzed Aryl Amination Mediated by Well Defined, N‐Heterocyclic Carbene (NHC)–Pd Precatalysts, PEPPSI
Author(s) -
Organ Michael G.,
AbdelHadi Mirvat,
Avola Stephanie,
Dubovyk Igor,
Hadei Niloufar,
Kantchev Eric Assen B.,
O'Brien Christopher J.,
Sayah Mahmoud,
Valente Cory
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200701621
Subject(s) - carbene , aryl , amination , chemistry , catalysis , combinatorial chemistry , palladium , organic chemistry , medicinal chemistry , alkyl
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.