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A Pd II Complex Bearing a Benzimidazole‐Derived Ligand with Potentially “Mesoionic and Remote” Character and Its Catalytic Activity
Author(s) -
Huynh Han Vinh,
Ong Hong Lee,
Bernhammer Jan C.,
Frison Gilles
Publication year - 2013
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201300334
Subject(s) - mesoionic , benzimidazole , ligand (biochemistry) , phenylacetylene , chemistry , palladium , catalysis , aryl , oxidative addition , tetrafluoroborate , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , receptor , biochemistry , alkyl , ionic liquid
The oxidative addition of palladium(0) to the C2‐protected 5‐bromo‐2‐methylbenzimidazolium tetrafluoroborate 3 affords the complex trans ‐[PdBr(bimy)(PPh 3 ) 2 ]BF 4 ( 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.