Experimental study demonstrates selective pentagonal ring closure in polycyclic aromatic hydrocarbons under hydrothermal conditions, suggesting an accessible route to strained cyclopenta-PAHs.
Platinum catalyzes the cleavage of two C−H bonds at the fjord position of a polycyclic aromatic hydrocarbon (PAH), and the subsequent C−C bond formation gives a cyclopenta-PAH. This post-construction of the pentagonal structure is energetically challenging and requires high temperatures. With water as the medium, it has been found that the monocyclization selectively occurs at a lower temperature. Fe2O3 is effective in suppressing side reactions. We found this reactivity in the Pt-catalyzed deuteration of dibenzo[g,p]chrysene in D2O. More information can be found in the Research Article by H. Tsuji and co-workers (DOI: 10.1002/chem.202400987).
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Hamaguchi et al. (2024) studied this question.
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