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Christian Torborg

Application of Novel Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions

Universität Rostock, 2009

Abstract: This thesis describes the application of 2-phosphino-N-aryl-heterocycles as ligands in Pd-catalyzed C–C, C–N and C–O bond forming reactions. Based on prior studies, 2-phosphino-N-arylindoles and -pyrrols were found to form efficient catalysts with Pd-salts in the Sonogashira coupling of (hetero)aryl bromides and the Pd-catalyzed monoarylation of ammonia. The novel imidazole-based phosphines were prepared after a modular synthesis and are stable towards air. They were employed in the Pd-catalyzed phenol synthesis, the Heck-Cassar coupling, and the Pd-catalyzed monoarylation of ammonia. Furthermore, mechanistic studies in the Pd-catalyzed hydroxylation were undertaken.

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