Synthesis of Large Hydroacenes and Related Compounds Using Gold(I) Catalysis

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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