The introduction of one alkyne moiety at the central carbon atom of the tripodal tribenzotriquinacene scaffold allows easy access to a great variety of apically functionalized derivatives. The spatially well-separated arrangement of different functional units on the convex face and outer rim was further proven by single-crystal X-ray studies. Subsequent modifications that feature a general protecting group-free strategy for the demethylation of protected catechols in the presence of a terminal alkyne group, an azide-alkyne Huisgen cycloaddition, and Sonogashira cross-coupling reactions showcase the high synthetic potential of this modular approach for tribenzotriquinacene derivatization.
Keywords: Sonogashira cross-coupling; alkynes; bowl-shaped molecules; click chemistry; tribenzotriquinacenes.
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