For the past two decades, our research group has been actively engaged in the synthesis of polycyclic aromatic hydrocarbons, such as acenes and their analogues, through gold(I)-catalyzed transformations. In this regard, in this Doctoral Thesis we have elaborated a new iterative synthesis for the preparation of higher unsubstituted hydroacenes, based on our previously developed gold(I)-catalyzed formal [4+2] cycloaddition of aryl-tethered 1,7-enynes. This approach enabled the formation of unprecedented hydroacenes, starting from tridecacene-H8, which gave rise to the parent acene after Au(111) surface-assisted dehydrogenation.
The precursors of acene derivatives belonging to diverse categories, such as indacenes, cyclobutadiene-containing acenes or heteroacenes have also been acquired by applying our gold(I)-catalyzed formal [4+2] cycloaddition to novel 1,7-enynes. One of the indacene derivatives was found to undergo a noteworthy intermolecular cycloaddition, rendering T-shaped molecules.
Finally, the Rh(III)-catalyzed ortho C–H alkynylation of aromatic aldehydes was investigated in the context of polyarene synthesis. Enabled by the formation of an imine as transient directing group, this transformation provided a wide variety of ynals, which were then successfully engaged in the preparation of substituted dibenzopentalenes, isoquinolines and indoles.
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