Recent findings on the skeletal rearrangement of polycyclic aromatics under oxidative and acidic conditions are envisioned to help development of these Scholl reactions into a more useful and versatile method for synthesizing polycyclic aromatics on the basis of rational design rather than luck.
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References
Scholl, R., Seer, C. & Weitzenböck, R. Perylen, ein hoch kondensierter aromatischer Kohlenwasserstoff C20H12. Ber. Dtsch. Chem. Ges. 43, 2202–2209 (1910).
Narita, A. et al. Synthesis of structurally well-defined and liquid-phase-processable graphene nanoribbons. Nat. Chem. 6, 126–132 (2014).
Zhai, L., Shukla, R. & Rathore, R. Oxidative C−C bond formation (Scholl reaction) with DDQ as an efficient and easily recyclable oxidant. Org. Lett. 11, 3474–3477 (2009).
Xia, Z., Pun, S. H., Chen, H. & Miao, Q. Synthesis of zigzag carbon nanobelts through Scholl reactions. Angew. Chem. Int. Ed. 60, 10311–10318 (2021).
Grzybowski, M., Sadowski, B., Butenschön, H. & Gryko, D. T. Synthetic applications of oxidative aromatic coupling — from biphenols to nanographenes. Angew. Chem. Int. Ed. 59, 2998–3027 (2020).
Zhai, L., Shukla, R., Wadumethrige, S. H. & Rathore, R. Probing the arenium-ion (protontransfer) versus the cation-radical (electron transfer) mechanism of Scholl reaction using DDQ as oxidant. J. Org. Chem. 75, 4748–4760 (2010).
Rempala, P., Kroulík, J. & King, B. T. Investigation of the mechanism of the intramolecular Scholl reaction of contiguous phenylbenzenes. J. Org. Chem. 71, 5067–5081 (2006).
Shen, C. et al. Oxidative cyclo-rearrangement of helicenes into chiral nanographenes. Nat. Commun. 12, 2786 (2021).
Qiu, Z. et al. Amplification of dissymmetry factors in π‑extended [7]- and [9]helicenes. J. Am. Chem. Soc. 143, 4661–4667 (2021).
Zhang, X. et al. Synthesis of extended polycyclic aromatic hydrocarbons by oxidative tandem spirocyclization and 1,2-aryl migration. Nat. Commun. 8, 15073 (2017).
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Miao, Q. Rearrangements come to Scholl. Nat Rev Chem 5, 602–603 (2021). https://doi.org/10.1038/s41570-021-00308-y
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DOI: https://doi.org/10.1038/s41570-021-00308-y
