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

Xuan Zhang, Zhanqiang Xu, Weili Si, Kazuaki Oniwa, Ming Bao, Yoshinori Yamamoto and Tienan Jin ()
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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
Tienan Jin: WPI-Advanced Institute for Materials Research (WPI-AIMR), Tohoku University

Nature Communications, 2017, vol. 8, issue 1, 1-8

Abstract: 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.

Date: 2017
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DOI: 10.1038/ncomms15073

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