A PdII Complex Bearing a Benzimidazole-Derived Ligand with Potentially "Mesoionic and Remote" Character and Its Catalytic Activity

Han Vinh Huynh (1) , Hong Lee Ong (1) , Jan C. Bernhammer (1) , Gilles Frison (2)

1 Department of chemistry
2 DCMR - Laboratoire des mécanismes réactionnels

The oxidative addition of palladium(0) to the C2-protected 5-bromo-2-methylbenzimidazolium tetrafluoroborate 3 affords the complex trans-[PdBr(bimy)(PPh3)2]BF4 (4), which is the first complex of an unprecedented benzimidazole-derived ligand (bimy) with a potentially "mesoionic and remote" character. DFT calculations revealed that the bimy ligand bridges the gap between the mesoionic pyrazolin-4-ylidene and the anionic phenyl ligand. A preliminary catalytic study revealed the promising activity of 4 in the Sonogashira coupling of aryl bromides with phenylacetylene.

Mots clés: Carbene ligands; Mesoionic compounds; Palladium; Cross-coupling; Density functional calculations

Domaines: Chimie théorique et/ou physique; Chimie de coordination; Catalyse

Han Vinh Huynh, Hong Lee Ong, Jan C. Bernhammer, Gilles Frison. A PdII Complex Bearing a Benzimidazole-Derived Ligand with Potentially "Mesoionic and Remote" Character and Its Catalytic Activity. European Journal of Inorganic Chemistry, 2013, pp.4654-4661. ⟨10.1002/ejic.201300334⟩. ⟨hal-00847374⟩