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First use of a palladium complex with a thiosemicarbazone ligand as catalyst precursor for the Heck reaction |
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| Authors: | Dimitra Kovala-Demertzi Paras N. Yadav Jerry P. Jasiski Ioannis D. Kostas |
| Affiliation: | a University of Ioannina, Department of Chemistry, Sector of Inorganic and Analytical Chemistry, 45110 Ioannina, Greece b Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2110, USA c National Hellenic Research Foundation, Institute of Organic and Pharmaceutical Chemistry, Vas. Constantinou 48, 116 35 Athens, Greece |
| Abstract: | A novel palladium complex with salicylaldehyde N(4)-ethylthiosemicarbazone has been synthesized and according to its crystal structure the ligand is bound to the metal in an O, N, S-terdentate coordination mode. This phosphorus-free system efficiently catalyzes the Heck reaction of aryl bromides (from electron-rich to electron-poor) with styrene under argon, with turnover numbers of up to 43,000, at 150 °C after 24 h, and with a selectivity toward trans-stilbenes ranging from 92 to 96%. In air, for activated aryl bromides and for a palladium concentration of 1 mM, the yields are essentially the same as those obtained when the reaction was performed under argon. |
| Keywords: | Thiosemicarbazone O, N, S-ligand Phosphine-free ligand Palladium complex Heck reaction Homogeneous catalysis |
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