Pd(II)-catalyzed Alkylation of Arenes and Hetarenes

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The project aims at a selective alkylation of hetarenes and arenes employing an alkyl halide and a Pd(II) catalyst. The additive norbornene should - as previously shown for indoles - induce a regioselective alkylation of NH-acidic heterocycles (e.g. pyrrole, imidazole, pyrazole, benzimidazole, 4-pyridone) via a strained palladacycle. Applications in natural product total synthesis should demonstrate the utility and brevity of the new method. Upon chiral modification of norbornene, stereoselective processes (enantiotopos differentiation, kinetic resolution) will be studied for the first time in this type of C-H activation reactions. In mechanistically related reactions, it is planned by an appropriate choice of the directing group to achieve an ortho selective or - upon addition of norbornene - a meta selective alkylation of aromatic hydrocarbons.