• dehydrogenative coupling
• 3-(hetero)arylindole
• Indole
• direct (hetero)arylation
• Csp2-H functionalization
• heteroarenes

Over the past thirty years, the landscape of organic synthesis has gained major attention by advent of the so-called “late-stage functionalization (LSF)” methodologies. Transition metal-catalysed C–H functionalization approaches pave the way for new retrosynthetic disconnections, meanwhile affording a considerable benefit from an economical and environmental point of view. Nevertheless, in literature heteroaryl-heteroaryl bond-constructing examples exploiting transition-metal-catalysed protocols are not frequent as expected. The reason lies within the intrinsic reactivity of these species due to binding of heteroatoms in the substrate and product to the metal centre, that can translate in a strong inhibitory effect.
The bi(hetero)aryl pattern represents a recurring structural motif found in bioactive natural products, materials science and in the pharmaceutical field, therefore developing a congenial protocol compatible with a wide spectrum of heteroarenes depicts a challenging goal for current organic chemists.
In the present Thesis work a preliminary study for the synthesis of 3-(hetero)arylindole derivatives has been carried out by means of researching efficient protocols of direct (hetero)arylation and dehydrogenative cross-coupling. In this kind of molecules, the presence of one or more heteroatoms allows a differentiation of the several aromatic C-H bonds, thus favouring the obtaining of the desired products through the Csp2-H functionalisation.