An efficient low-temperature Stille-Migita cross-coupling reaction for heteroaromatic compounds by Pd-PEPPSI-IPent.
The reactivity of Pd-PEPPSI (Pyridine, Enhanced, Precatalyst, Preparation, Stabilization, and Initiation) precatalysts in the Stille-Migita cross-coupling reaction between heteroaryl stannanes and aryl or heteroaryl halides was evaluated. In general, Pd-PEPPSI-IPent (IPent=diisopentylphenylimidazolium derivative) demonstrated high efficiency over a variety of challenging aryl or heteroaryl halides with thiophene-, furan-, pyrrole-, and thiazole-based organostannanes when compared with Pd-PEPPSI-IPr (IPr=diisopropylphenylimidazolium derivative). The transformations proceeded at appreciably lower temperatures (30-80 degrees C) than triarylphosphine-based Pd catalysts, improving the scope of this useful carbon-carbon bond-forming process.
Dowlut
Meenakshi
M
Department of Chemistry, York University, 4700 Keele Street, Toronto, ON, M3J 1P3, Canada.
Mallik
Debasis
D
Organ
Michael G
MG
D002384:Catalysis; D003432:Cross-Linking Reagents; D006571:Heterocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013329:Structure-Activity Relationship; D013696:Temperature
D003432:Cross-Linking Reagents; D006571:Heterocyclic Compounds; D009942:Organometallic Compounds; D011725:Pyridines; D012997:Solvents; D010165:Palladium