Alkyl Tosylates and Iodides as Reactive Partners with Low Valent Pd Complexes
Description
One of the most challenging problems in modern catalytic chemistry is the upcycling and degradation of synthetic polymers. Specifically, the activation of the inert carbon-carbon bond proves to be difficult due to the stability of the linkage between carbon atoms and weak bond strength of the catalytic intermediates between carbon and a metal center. In this research, we aim to utilize Pd(0) complexes for the oxidative addition of alkyl groups and investigate their reactivity. By altering the ligands bound to palladium, the solvent and the reactivity of the leaving group attached to the substrates, the goal is to apply these insights to the activation of carbon-carbon bonds. To this end, phenethyl tosylate was synthesized. Phenethyl tosylate is an organic molecule with a good leaving group suitable for oxidative addition to a Pd(0) complex. The reactions containing Pd are conducted using air-free synthetic chemistry techniques. The chemical product analysis is conducted with nuclear magnetic resonance (NMR) spectroscopy of 1H- and 31P-nuclei and gas chromatography-mass spectrometry. The palladium precursor tris(dibenzylideneacetone)dipalladium (Pd2(dba)3) was subject to react with triphenylphosphine and phenethyl tosylate. Initial results yielded a dependence of the oxidative addition on the solvent used. In the nonpolar toluene, a reaction in solution failed to occur even after heating the reaction to 80 °C. In the more polar solvent tetrahydrofuran (THF), the formation of 2 species was observed with 1H-NMR analysis. The chemical composition of these products and the reactivities with further substrates in different solvents are going to be investigated in future experiments.
Alkyl Tosylates and Iodides as Reactive Partners with Low Valent Pd Complexes
One of the most challenging problems in modern catalytic chemistry is the upcycling and degradation of synthetic polymers. Specifically, the activation of the inert carbon-carbon bond proves to be difficult due to the stability of the linkage between carbon atoms and weak bond strength of the catalytic intermediates between carbon and a metal center. In this research, we aim to utilize Pd(0) complexes for the oxidative addition of alkyl groups and investigate their reactivity. By altering the ligands bound to palladium, the solvent and the reactivity of the leaving group attached to the substrates, the goal is to apply these insights to the activation of carbon-carbon bonds. To this end, phenethyl tosylate was synthesized. Phenethyl tosylate is an organic molecule with a good leaving group suitable for oxidative addition to a Pd(0) complex. The reactions containing Pd are conducted using air-free synthetic chemistry techniques. The chemical product analysis is conducted with nuclear magnetic resonance (NMR) spectroscopy of 1H- and 31P-nuclei and gas chromatography-mass spectrometry. The palladium precursor tris(dibenzylideneacetone)dipalladium (Pd2(dba)3) was subject to react with triphenylphosphine and phenethyl tosylate. Initial results yielded a dependence of the oxidative addition on the solvent used. In the nonpolar toluene, a reaction in solution failed to occur even after heating the reaction to 80 °C. In the more polar solvent tetrahydrofuran (THF), the formation of 2 species was observed with 1H-NMR analysis. The chemical composition of these products and the reactivities with further substrates in different solvents are going to be investigated in future experiments.