Skip to main content
SpringerLink
Log in

POLYCYCLIC AROMATICS

Rearrangements come to Scholl

  • News & Views
  • Published:

From Nature Reviews Chemistry

View current issue Sign up to alerts

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1: Scholl reactions with and without rearrangement.

References

  1. Scholl, R., Seer, C. & Weitzenböck, R. Perylen, ein hoch kondensierter aromatischer Kohlenwasserstoff C20H12. Ber. Dtsch. Chem. Ges. 43, 2202–2209 (1910).

    Article  CAS  Google Scholar 

  2. Narita, A. et al. Synthesis of structurally well-defined and liquid-phase-processable graphene nanoribbons. Nat. Chem. 6, 126–132 (2014).

    Article  CAS  Google Scholar 

  3. 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).

    Article  CAS  Google Scholar 

  4. 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).

    Article  CAS  Google Scholar 

  5. 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).

    Article  CAS  Google Scholar 

  6. 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).

    Article  CAS  Google Scholar 

  7. 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).

    Article  CAS  Google Scholar 

  8. Shen, C. et al. Oxidative cyclo-rearrangement of helicenes into chiral nanographenes. Nat. Commun. 12, 2786 (2021).

    Article  CAS  Google Scholar 

  9. Qiu, Z. et al. Amplification of dissymmetry factors in π‑extended [7]- and [9]helicenes. J. Am. Chem. Soc. 143, 4661–4667 (2021).

    Article  CAS  Google Scholar 

  10. Zhang, X. et al. Synthesis of extended polycyclic aromatic hydrocarbons by oxidative tandem spirocyclization and 1,2-aryl migration. Nat. Commun. 8, 15073 (2017).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China

    Qian Miao

Authors
  1. Qian Miao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Qian Miao.

Ethics declarations

Competing interests

The author declares no competing interests.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Miao, Q. Rearrangements come to Scholl. Nat Rev Chem 5, 602–603 (2021). https://doi.org/10.1038/s41570-021-00308-y

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41570-021-00308-y

  • Springer Nature Limited

Search

Navigation