1370328-75-8Relevant academic research and scientific papers
Synthetic, structural, and catalytic studies of well-defined allyl 1,2,3-triazol-5-ylidene (tzNHC) palladium complexes
Terashima, Takahiro,Inomata, Sayuri,Ogata, Kenichi,Fukuzawa, Shin-Ichi
, p. 1387 - 1393 (2012/05/31)
A series of allyl 1,2,3-triazol-5-ylidene (tzNHC) palladium complexes was prepared, and the structures of the complexes were fully characterized by NMR and X-ray diffraction analyses. The donor properties of these ligands were evaluated by studying the vibrational spectra of their carbonyliridium complexes and their X-ray photoelectron spectra. These evaluations showed that the structures of the tzNHC palladium complexes are almost identical to those of the corresponding imidazole carbene palladium complexes, and that the tzNHC ligands have stronger donor properties than the imidazole carbene ligands. The relationship between catalytic activity and structure was examined by carrying out a room-temperature Suzuki-Miyaura coupling reaction, and the cinnamylpalladium complex bearing 1,4-bis(2,6-diisopropylphenyl)-3-methyl-1,2,3- triazol-5-ylidene (TPr) was found to be the most active catalyst. (cinnamyl)(TPr)PdCl showed high activity in the room-temperature reaction performed with aryl chlorides regardless of the electronic and steric properties of the substituents, and was effective in reactions with sterically crowded arylboronic acids. A series of (η3-allyl)palladium complexes bearing 1,2,3-triazole carbene (tzNHC) ligands has been prepared and characterized. The donor properties of tzNHC ligands are stronger than those of imidazole carbene ligands. The [1,4-bis(2,6-diisopropylphenyl)-3-methyl-1,2,3- triazol-5-ylidene](cinnamyl)PdCl complex shows high activity in the room-temperature Suzuki-Miyaura coupling reaction with aryl chlorides.
