Easily prepared air- and moisture-stable Pd-NHC (NHC=N-heterocyclic carbene) complexes: a reliable, user-friendly, highly active palladium precatalyst for the Suzuki-Miyaura reaction.
The synthesis of NHC-PdCl(2)-3-chloropyridine (NHC=N-heterocyclic carbene) complexes from readily available starting materials in air is described. The 2,6-diisopropylphenyl derivative was found to be highly catalytically active in alkyl-alkyl Suzuki and Negishi cross-coupling reactions. The synthesis, ease-of-use, and activity of this complex are substantial improvements over in situ catalyst generation and all current Pd-NHC complexes. The utilization of complex 4 led to the development of a reliable, easily employed Suzuki-Miyama protocol. Employing various reaction conditions allowed a large array of hindered biaryl and drug-like heteroaromatic compounds to be synthesized without difficulty.
O'Brien
Christopher J
CJ
Department of Chemistry, York University, 4700 Keele Street, Toronto, ON M3J 1P3, Canada.
Kantchev
Eric Assen B
EA
Valente
Cory
C
Hadei
Niloufar
N
Chass
Gregory A
GA
Lough
Alan
A
Hopkinson
Alan C
AC
Organ
Michael G
MG