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Synthesis of extended polycyclic aromatic hydrocarbons by oxidative tandem spirocyclization and 1,2-aryl migration

Author

Listed:
  • Xuan Zhang

    (WPI-Advanced Institute for Materials Research (WPI-AIMR), Tohoku University)

  • Zhanqiang Xu

    (WPI-Advanced Institute for Materials Research (WPI-AIMR), Tohoku University)

  • Weili Si

    (WPI-Advanced Institute for Materials Research (WPI-AIMR), Tohoku University)

  • Kazuaki Oniwa

    (WPI-Advanced Institute for Materials Research (WPI-AIMR), Tohoku University)

  • Ming Bao

    (State Key Laboratory of Fine Chemicals, Dalian University of Technology)

  • Yoshinori Yamamoto

    (WPI-Advanced Institute for Materials Research (WPI-AIMR), Tohoku University
    State Key Laboratory of Fine Chemicals, Dalian University of Technology)

  • Tienan Jin

    (WPI-Advanced Institute for Materials Research (WPI-AIMR), Tohoku University
    State Key Laboratory of Fine Chemicals, Dalian University of Technology)

Abstract

The extended polycyclic aromatic hydrocarbons (PAHs) have received significant interdisciplinary attention due to their semiconducting applications in diverse organic electronics as well as intriguing structural interests of well-defined graphene segments. Herein, a highly efficient oxidative spirocyclization and 1,2-aryl migration tandem synthetic method for the construction of extended polyaromatic hydrocarbons (PAHs) has been developed. The CuCl-catalyst/PhCO3 tBu or DDQ oxidation system in the presence of trifluoroacetic acid enables the selective single-electron oxidation to take place preferentially at the more electron-rich alkene moiety of o-biphenylyl-substituted methylenefluorenes, giving rise to the subsequent tandem process. A variety of structurally diverse extended PAHs including functionalized dibenzo[g,p]chrysenes, benzo[f]naphtho[1,2-s]picene, hexabenzo[a,c,fg,j,l,op]tetracene, tetrabenzo[a,c,f,m]phenanthro[9,10-k]tetraphene, tetrabenzo[a,c,f,k]phenanthro[9,10-m]tetraphene, tetrabenzo[a,c,f,o]phenanthro[9,10-m]picene and S-type helicene have been readily synthesized.

Suggested Citation

  • Xuan Zhang & Zhanqiang Xu & Weili Si & Kazuaki Oniwa & Ming Bao & Yoshinori Yamamoto & Tienan Jin, 2017. "Synthesis of extended polycyclic aromatic hydrocarbons by oxidative tandem spirocyclization and 1,2-aryl migration," Nature Communications, Nature, vol. 8(1), pages 1-8, April.
    • Handle: RePEc:nat:natcom:v:8:y:2017:i:1:d:10.1038_ncomms15073
    DOI: 10.1038/ncomms15073
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