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A strategy for the preparation of cyclic polyarenes based on single electron transfer-promoted photocyclization reactions

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Abstract

Single electron transfer (SET)-promoted photocyclization reactions of substrates comprised of benzylsilane tethered to phthalimides were subjected to an exploratory study in order to probe a new approach for the preparation of cyclic polyarenes. The results show that UV irradiation of the substrates leads to efficient photochemical reactions that are initiated by SET from benzylsilane moieties to the excited phthalimide acceptor. Ensuing desilylation reactions of the benzylsilane cation radical moieties in the intermediate zwitterionic biradicals and proton transfer gives biradical precursors of the cyclic polyarene products. The observations made in this effort suggests that SET photochemical methods, which have been employed earlier to generate cyclic poly-ethers, -thioethers and -amides, serve as a useful method to access potentially interesting macrocyclic targets.

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Acknowledgments

This investigation was supported financially by the National Research Foundation of Korea Grant to U.C.Y. supported by the Korean Government (KRF-2008-521-C00156). In addition, we offer our congratulation to Professor Kazuhiko Mizuno on the excellent career he has had in the academic profession and for the important scientific contributions he has made to the fields of organic chemistry and organic photochemistry.

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Authors and Affiliations

  1. Department of Chemistry, and Chemistry Institute for Functional Materials, Pusan National University, Busan, 609-735, Korea

    Hea Jung Park, Jung Hei Choi, Byeol Na Park & Ung Chan Yoon

  2. Department of Chemistry, Yeungnam University, Gyeongsan, Gyeongbuk, 712-749, Korea

    Dae Won Cho

  3. Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, NM, 87131, USA

    Patrick S. Mariano

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  1. Hea Jung Park
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  2. Jung Hei Choi
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  3. Byeol Na Park
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  4. Ung Chan Yoon
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  6. Patrick S. Mariano
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Correspondence to Ung Chan Yoon or Dae Won Cho.

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Park, H.J., Choi, J.H., Park, B.N. et al. A strategy for the preparation of cyclic polyarenes based on single electron transfer-promoted photocyclization reactions. Res Chem Intermed 38, 847–862 (2012). https://doi.org/10.1007/s11164-011-0422-8

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