Pd-catalyzed aryl amination mediated by well defined, N-heterocyclic carbene (NHC)-Pd precatalysts, PEPPSI.
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.
Organ
Michael G
MG
Chemistry Department, York University, 4700 Keele Street, Toronto, M3J 1P3, Canada. organ@yorku.ca
Abdel-Hadi
Mirvat
M
Avola
Stephanie
S
Dubovyk
Igor
I
Hadei
Niloufar
N
Kantchev
Eric Assen B
EA
O'Brien
Christopher J
CJ
Sayah
Mahmoud
M
Valente
Cory
C
D000586:Amination; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006838:Hydrocarbons / Q000737:chemistry; D008024:Ligands; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry; D013696:Temperature
D006571:Heterocyclic Compounds; D006838:Hydrocarbons; D008024:Ligands; D010720:Phosphines; C030011:carbene; D010165:Palladium; D008697:Methane