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Synthesis of 1,1′-binaphthyl derivatives by Miyaura-Suzuki cross-coupling in cholesteric liquid crystal phase

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Abstract

We synthesized 1,1′-binaphthyl and 2-substituted-1,1′-binaphthyl by the Miyaura-Suzuki cross-coupling reaction in cholesteric liquid crystal (CLC) media. The 1H and 13C NMR and UV–Vis absorption spectra of the compounds thus prepared were examined. The liquid crystallinity of the CLC media before and after the reaction was confirmed by differential scanning calorimetry, polarizing optical microscopy, and visual contact in order to characterize the reaction in a CLC phase.

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References

  1. Kozlowski MC, Morgan BJ, Linton EC (2009) Chem Soc Rev 38:3193

    Article  CAS  Google Scholar 

  2. Dong J, Kawabata K, Seino T, Yang F, Goto H (2013) Liq Cryst 40:1455

    Article  CAS  Google Scholar 

  3. Miyaura N, Suzuki A (1995) Chem Rev 95:2457

    Article  CAS  Google Scholar 

  4. Castanet AS, Colobert F, Broutin PE, Obringer M (2002) Tetrahedron Asymmetry 13:659

    Article  CAS  Google Scholar 

  5. Yin J, Rainka MP, Zhang XX, Buchwald SL (2002) J Am Chem Soc 124:1162

    Article  CAS  Google Scholar 

  6. Pu L (1998) Chem Rev 98:2405

    Article  CAS  Google Scholar 

  7. Wang Y, Li Q (2012) Adv Mater 24:1926

    Article  CAS  Google Scholar 

  8. Huang WS, Hu QS, Pu L (1999) J Org Chem 64:7940

    Article  CAS  Google Scholar 

  9. Goto H (2007) Macromolecules 40:1377

    Article  CAS  Google Scholar 

  10. Iseki T, Kawabata K, Nimori S, Goto H (2014) Synth Met 187:217

    Article  CAS  Google Scholar 

  11. Li Y, Xue C, Wang M, Urbas A, Li Q (2013) Angew Chem Int Ed 52:13703

    Article  CAS  Google Scholar 

  12. Verbit L, Halbert TR, Patterson RB (1975) J Org Chem 40:1649

    Article  CAS  Google Scholar 

  13. Saeva FD, Sharpe PE, Olin GR (1975) J Am Chem Soc 97:204

    Article  CAS  Google Scholar 

  14. Iseki T, Kawabata K, Kawashima H, Goto H (2014) Polymer 55:66

    Article  CAS  Google Scholar 

  15. Kawabata K, Takeguchi M, Goto H (2013) Macromolecules 46:2078

    Article  CAS  Google Scholar 

  16. Goto H (2013) RSC Adv 3:6347

    Article  CAS  Google Scholar 

  17. Wang L, Lu W (2009) Org Lett 11:1079

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We would like to thank the Glass Work Shop and Chemical Analysis Division Research Facility Center for Science and Technology of the University of Tsukuba for glass work and NMR, GC–MS, and DSC measurements.

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Correspondence to Hiromasa Goto.

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Iseki, T., Goto, H. Synthesis of 1,1′-binaphthyl derivatives by Miyaura-Suzuki cross-coupling in cholesteric liquid crystal phase. Monatsh Chem 145, 1145–1149 (2014). https://doi.org/10.1007/s00706-014-1199-4

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  • DOI: https://doi.org/10.1007/s00706-014-1199-4

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