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Efficient Construction of Highly-fused Diperylene Bismides by Cu/Oxalic Diamide-promoted Zipper-mode Double C-H Activation

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Abstract

Copper/oxalic diamide-promoted dimerization of tetrachlorinated perylene bisimide to construct highly-fused diperylene bisimides through Ullmann coupling and zipper-mode double C-H activation has been developed in this study. This one-step reaction combining homocoupling with C-H activation proceeded smoothly under the action of inexpensive metal-ligand system. This protocol is expected to expand the available synthetic tools for condensed ring systems of perylene bisimide(PBIs).

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References

  1. Gupta R. K., Sudhakar A. A., Langmuir, 2019, 35, 2455

    Article  CAS  PubMed  Google Scholar 

  2. Chal P., Shit A., Nandi A. K., Chemistry Select, 2018, 3, 3993

    CAS  Google Scholar 

  3. Jones B. A., Ahrens M. J., Yoon M., Facchetti A., Marks T. J., Wasielewski M. R., Angew. Chem., Int. Ed., 2004, 43, 6363

    Article  CAS  Google Scholar 

  4. Lv A., Puniredd S. R., Zhang J., Li Z., Zhu H., Jiang W., Dong H., He Y., Jiang L., Li Y., Pisula W., Meng Q., Hu W., Wang Z., Adv. Mater., 2012, 24, 2626

    Article  CAS  PubMed  Google Scholar 

  5. Li Y., Wang Z., Qian H., Shi Y., Hu W., Org. Lett., 2008, 10, 529

    Article  CAS  PubMed  Google Scholar 

  6. Gsänger M., Oh J. H., Könemann M., Höffken H. W., Krause A. M., Bao Z., Würthner F., Angew. Chem., Int. Ed., 2010, 49, 740

    Article  CAS  Google Scholar 

  7. Meng D., Liu G., Xiao C., Shi Y., Zhang L., Jiang L., Baldridge K. K., Li Y., Siegel J. S., Wang Z., J. Am. Chem. Soc., 2019, 141, 5402

    Article  CAS  PubMed  Google Scholar 

  8. Xin R., Feng J., Zeng C., Jiang W., Zhang L., Meng D., Ren Z., Wang Z., Yan S., ACS Appl. Mater. Interfaces, 2017, 9, 2739

    Article  CAS  PubMed  Google Scholar 

  9. Liu X., Du X., Wang J., Duan C., Tang X., Heumueller T., Liu G., Li Y., Wang Z., Wang J., Liu F., Li N., Brabec C. J., Huang F., Cao Y., Adv. Energy Mater., 2018, 8, 1801699

    Article  CAS  Google Scholar 

  10. Gupta R. K., Dey A., Singh A., Iyer P. K., Sudhakar A. A., ACS Appl. Electron. Mater., 2019, 1, 1378

    Article  CAS  Google Scholar 

  11. Lin Z., Li C., Meng D., Li Y., Wang Z., Chem.-Asian J., 2016, 11, 2695

    Article  CAS  PubMed  Google Scholar 

  12. Cotlet M., Vosch T., Habuchi S., Well T., Müllen K., Hofkens J., Schryver F., J. Am. Chem. Soc., 2005, 127, 9760

    Article  CAS  PubMed  Google Scholar 

  13. Schönamsgruber J., Hirsch A., Eur. J. Org. Chem., 2015, 2015, 2167

    Article  CAS  Google Scholar 

  14. Yan Q., Zhao D., Org. Lett., 2009, 11, 3426

    Article  CAS  PubMed  Google Scholar 

  15. Qian H., Wang Z., Yue W., Zhu D., J. Am. Chem. Soc., 2007, 129, 10664

    Article  CAS  PubMed  Google Scholar 

  16. Shi Y., Qian H., Li Y., Yue W., Wang Z., Org. Lett., 2008, 10, 2337

    Article  CAS  PubMed  Google Scholar 

  17. Qian H., Negri F., Wang C., Wang Z., J. Am. Chem. Soc., 2008, 130, 17970

    Article  CAS  PubMed  Google Scholar 

  18. Zhen Y., Qian H., Xiang J., Qu J., Wang Z., Org. Lett., 2009, 11, 3084

    Article  CAS  PubMed  Google Scholar 

  19. Zhen Y., Wang C., Wang Z., Chem. Commun., 2010, 46, 1926

    Article  CAS  Google Scholar 

  20. Lu X., Dong H., He P., Zhang X., Liu J., Meng Q., Jiang L., Wang Z., Zhen Y., Hu W., Asian J. Org. Chem., 2013, 2, 558

    Article  CAS  Google Scholar 

  21. Zhang J., Tan L., Jiang W., Hu W., Wang Z., J. Mater. Chem. C, 2013, 1, 3200

    Article  CAS  Google Scholar 

  22. Zhou T., Li B., Wang B., Chem. Commun., 2017, 53, 6343

    Article  CAS  Google Scholar 

  23. Naota T., Takaya H., Murahashi S. I., Chem. Rev., 1998, 98, 2599

    Article  CAS  PubMed  Google Scholar 

  24. Chen H., Schlecht S., Semple T. C., Hartwig J. F., Science, 2000, 287, 1995

    Article  CAS  PubMed  Google Scholar 

  25. Key H. M., Dydio P., Clark D. S., Hartwig J. F., Nature, 2016, 534, 534

    Article  CAS  PubMed  Google Scholar 

  26. Gandeepan P., Müller T., Zell D., Cera G., Warratz S., Ackermann L., Chem. Rev., 2019, 119, 2192

    Article  CAS  PubMed  Google Scholar 

  27. Sun C. L., Li B. J., Shi Z. J., Chem. Commun., 2010, 46, 677

    Article  CAS  Google Scholar 

  28. Wang H., Pesciaioli F., Oliveira C. A., Warratz S., Ackermann L., Angew. Chem., Int. Ed., 2017, 56, 15063

    Article  CAS  Google Scholar 

  29. Liu X., Mao G., Qiao J., Xu C., Liu H., Ma J., Sun Z., Chu W., Org. Chem. Front., 2019, 6, 1189

    Article  CAS  Google Scholar 

  30. Phipps R. J., Gaunt M. J., Science, 2009, 323, 1593

    Article  CAS  PubMed  Google Scholar 

  31. Chen Z., Jiang Y., Zhang L., Guo Y., Ma D., J. Am. Chem. Soc., 2019, 141, 3541

    Article  CAS  PubMed  Google Scholar 

  32. Lewis E. A., Marcinkowski M. D., Murphy C. J., Liriano M. L., Therrien A. J., Pronschinske A., Sykes E. C. H., Chem. Comm., 2017, 53, 7816

    Article  CAS  PubMed  Google Scholar 

  33. Zhang H., Cai Q., Ma D., J. Org. Chem., 2005, 70, 5164

    Article  CAS  PubMed  Google Scholar 

  34. Cai Q., He G., Ma D., J. Org. Chem., 2006, 71, 5268

    Article  CAS  PubMed  Google Scholar 

  35. Cai Q., Zou B., Ma D., Angew. Chem., Int. Ed., 2006, 45, 1276

    Article  CAS  Google Scholar 

  36. Xia S., Gan L., Wang K., Li Z., Ma D., J. Am. Chem. Soc., 2016, 138, 13493

    Article  CAS  PubMed  Google Scholar 

  37. Ma D., Cai Q., Acc. Chem. Res., 2008, 41, 1450

    Article  CAS  PubMed  Google Scholar 

  38. Nunomoto S., Kawakami Y., Yamashita Y., J. Org. Chem., 1983, 48, 1912

    Article  CAS  Google Scholar 

  39. Li H., Cai G. X., Shi Z. J., Dalton Transactions, 2010, 39, 10442

    Article  CAS  PubMed  Google Scholar 

  40. Posner G. H., An Introduction to Synthesis Using Organocopper Reagents, Wiley, Weinheim, 1980

    Google Scholar 

  41. Sharma P., Rohilla S., Jain N., J. Org. Chem., 2015, 80, 4116

    Article  CAS  PubMed  Google Scholar 

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Authors and Affiliations

  1. School of Ocean Science and Biochemistry Engineering, Fuqing Branch of Fujian Normal University, Fuzhou, 350300, P. R. China

    Xiuqiang Lu & Hui Lin

  2. Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, P. R. China

    Xiuqiang Lu, Yonggang Zhen & Huanli Dong

  3. Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, School of Sciences, Tianjin University, Tianjin, 300072, P. R. China

    Xiaotao Zhang & Wenping Hu

Authors
  1. Xiuqiang Lu
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  2. Hui Lin
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  3. Yonggang Zhen
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  4. Huanli Dong
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  5. Xiaotao Zhang
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  6. Wenping Hu
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Corresponding authors

Correspondence to Yonggang Zhen, Huanli Dong or Wenping Hu.

Additional information

Supported by the National Natural Science Foundation of China(Nos.51503037, 51822308, 51733004, 21661132006), the Program for New Century Excellent Talents in Fujian Province Universities, China, the Fund of the Youth Innovation Promotion Association of the Chinese Academy of Sciences and the Education and Scientific Research Project for Young and Middle-aged Teachers in Fujian Province, China (No.JT180633)..

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40242_2020_9051_MOESM1_ESM.pdf

Efficient Construction of Highly-fused Diperylene Bismides by Cu/Oxalic Diamide-promoted Zipper-mode Double C-H Activation

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Lu, X., Lin, H., Zhen, Y. et al. Efficient Construction of Highly-fused Diperylene Bismides by Cu/Oxalic Diamide-promoted Zipper-mode Double C-H Activation. Chem. Res. Chin. Univ. 36, 110–114 (2020). https://doi.org/10.1007/s40242-020-9051-3

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  • DOI: https://doi.org/10.1007/s40242-020-9051-3

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