1. Synthesis of Polycyclic Heteroaromatic Hydrocarbons (Hetero-PAHs)

Polycyclic heteroaromatic hydrocarbons (hetero-PAHs) are of considerable importance in the field of medicinal chemistry (e.g., cancerostatic activity) and of materials science (e.g., for OLED or semiconductor applications). Palladium-catalyzed cross-coupling and cyclization reactions allow for a convenient and selective synthesis of a great variety of hetero-PAHs. The projects are driven both by the development of new reactions and by the synthesis of new target molecules and their properties.

1.1 Cross-Coupling / CH-Activation Reactions

Abstract: The combination of Pd-catalyzed cross-coupling with CH-arylation reactions allow for the synthesis of various hetero-PAHs with interesting optical, electronic or pharmacological properties. Simple nitro-substituted heterocycles undergo Pd-catalyzed CH-arylation reactions with excellent regioselectivity.

Review: Synlett 2024, DOI: 10.1055/s-0042-1751540.

Period of investigation: 2011 - Today

Keywords: Pd catalysis; heterocycles

1.2 Cross-Coupling / Alkyne-Carbonyl-Metathesis (ACM) Reactions

Abstract: The combination of Pd-catalyzed C-C Cross-coupling with alkyne-carbonyl-metathesis (ACM) reactions allows for the synthesis of a variety of benzoyl-substituted hetero-PAHs.

Review: Synlett 2024, DOI: 10.1055/s-0042-1751513.

Period of investigation: 2016 - Today

Keywords: alkyne-carbonyl-metathesis; Pd-catalysis; heterocycles

1.3 Cross-Coupling / Cycloisomerization Reactions

Abstract: The combination of Pd-catalyzed C-C Cross-coupling with cycloisomerization reactions allows for the synthesis of a variety of various hetero-PAHs with interesting optical, electronic or pharmacological properties.

Review: Synlett 2022, 33, 1707–1715.

Period of investigation: 2016 - Today

Keywords: Pd-catalysis; heterocycles

1.4 Cross-Coupling / Hydroamination Reactions

Abstract: The combination of Pd-catalyzed C-C Cross-coupling with hydroamination reactions of alkynes allows for the synthesis of a variety of various polycyclic aromatic heterocycles with interesting optical, electronic or pharmacological properties.

Review: Synlett 2022, 33, 1596-1606.

Period of investigation: 2010 - Today

Keywords: Pd-catalysis; heterocycles

1.5 Cross-Coupling / Twofold C-N Coupling Reactions

Abstract: The combination of Pd-catalyzed C-C Cross-coupling with twofold C-N coupling reactions allows for the synthesis of a variety of various hetero-PAHs with interesting optical, electronic or pharmacological properties.

Review: Synlett 2022, 33, 1215-1226.

Period of investigation: 2012 - Today

Keywords: Pd-catalysis; heterocycles