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New Adducts of Triphenylboroxine and Bis-pyridines: Syntheses and Crystal Structures of (Ph3B3O3)(η 1-4,4′-bpy), (Ph3B3O3)2(μ-4,4′-bpy) and (Ph3B3O3)2(μ-bpe)

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Abstract

The treatment of phenylboronic acid PhB(OH)2 with 4,4′-bipyridine (4,4′-bpy) in a 3:1 ratio afforded adduct [(Ph3B3O3)(η 1-4,4′-bpy)] (1), whereas the reaction of PhB(OH)2 with 4,4′-bpy in a 6:1 ratio afforded adduct [(Ph3B3O3)2(μ-4,4′-bpy)] (2). Similarly, the reaction of PhB(OH)2 with trans-1,2-bis(4-pyridyl)ethylene (bpe) in a 6:1 ratio gave bpe bridged adduct [(Ph3B3O3)2(μ-bpe)] (3). The crystal structures of 1·½C6H6, 2·2C7H8, 2·C6H14, and 3·C6H6, along with other spectroscopic properties are reported. The weak N···H–C hydrogen-bonds exist in the one-dimensional chains of 1·½C6H6.

Graphical Abstract

Treatment of PhB(OH)2 with 4,4′-bpy or bpe under different conditions afforded three new adducts [(Ph3B3O3)(η 1-4,4′-bpy)] (1), [(Ph3B3O3)2(μ-4,4′-bpy)] (2) and [(Ph3B3O3)2(μ-bpe)] (3) through the B–N dative bonds.

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References

  1. EI-Kaderi HM, Hunt JR, Mendoza-Cortés JL, Côté AP, Taylor RE, O’Keeffe M, Yaghi OM (2007) Science 316:268–272

    Article  Google Scholar 

  2. Côté AP, EI-Kaderi HM, Furukawa H, Hunt JR, Yaghi OM (2007) J Am Chem Soc 129:12914–12915

    Article  Google Scholar 

  3. Han SS, Furukawa H, Yaghi OM, Goddard WA (2008) J Am Chem Soc 130:11580–11581

    Article  CAS  Google Scholar 

  4. Furukawa H, Yaghi OM (2009) J Am Chem Soc 131:8875–8883

    Article  CAS  Google Scholar 

  5. Korich AL, Iovine PM (2010) Dalton Trans 39:1423–1431

    Article  CAS  Google Scholar 

  6. Azuma T, Murata A, Kobayashi Y, Inokuma T, Takemoto Y (2014) Org Lett 16:4256–4259

    Article  CAS  Google Scholar 

  7. Sheepwash E, Krampl V, Scopelliti R, Sereda O, Neels A, Severin K (2011) Angew Chem Int Ed 50:3034–3037

    Article  CAS  Google Scholar 

  8. Icli B, Solari E, Riis-Johannessen T, Schenk K, Filinchuk Y, Scopelliti R, Severin K (2011) Chem Sci 2:1719–1721

    Article  CAS  Google Scholar 

  9. Icli B, Solari E, Kilbas B, Scopelliti R, Severin K (2012) Chem Eur J 18:14867–14874

    Article  CAS  Google Scholar 

  10. Feng X, Chen L, Dong Y, Jiang D (2011) Chem Commun 47:1979–1981

    Article  CAS  Google Scholar 

  11. Yalpani M, Boese R (1983) Eur J Inorg Chem 116:3347–3358

    CAS  Google Scholar 

  12. Beckmann J, Dakternieks D, Duthie A, Lim AEK, Tiekink ERT (2001) J Organomet Chem 633:149–156

    Article  CAS  Google Scholar 

  13. Beckett MA, Strickland GC, Varma KS, Hibbs DE, Hursthouse MB, Malik KMA (1995) Polyhedron 14:2623–2630

    Article  CAS  Google Scholar 

  14. Beckett MA, Strickland GC, Varma KS, Hibbs DE, Hursthouse MB, Malik KMA (1997) J Organomet Chem 535:33–41

    Article  CAS  Google Scholar 

  15. Wu QG, Wu G, Brancaleon L, Wang S (1999) Organometallics 18:2553–2556

    Article  CAS  Google Scholar 

  16. Ferguson G, Lough AJ, Sheehan JP, Spalding TR (1990) Acta Crystallogr C 46:2390–2392

    Article  Google Scholar 

  17. Beckett MA, Coles SJ, Light ME, Fischer L, Stiefvater-Thomas BM, Varma KS (2006) Polyhedron 25:1011–1016

    Article  CAS  Google Scholar 

  18. Beckett MA, Hibbs DE, Hursthouse MB, Owen P, Malik KMA, Varma KS (1998) Main Group Chem 2:251–258

    Article  CAS  Google Scholar 

  19. Saint S (1998) SMART and SAINT+ for windows NT version 6.02a. Bruker Analytical X-ray Instruments Inc., Madison

    Google Scholar 

  20. Sheldrick GM (1996) SADABS. University of Göttingen, Germany

    Google Scholar 

  21. Sheldrick GM (1997) SHELXTL software reference manual, version 5.1. Bruker AXS Inc., Madison

    Google Scholar 

  22. Boese R, Polk M, Bläser D (1987) Angew Chem Int Ed Engl 76:245–246

    Article  Google Scholar 

  23. Brock CP, Minton RP, Niedenzu K (1987) Acta Crystallogr C43:1775–1779

    CAS  Google Scholar 

  24. Bolte M (2004) Private communication

Download references

Acknowledgments

This project was supported by the Natural Science Foundation of China (90922008).

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Correspondence to Qian-Feng Zhang.

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Wang, YJ., Jia, AQ., Chen, XS. et al. New Adducts of Triphenylboroxine and Bis-pyridines: Syntheses and Crystal Structures of (Ph3B3O3)(η 1-4,4′-bpy), (Ph3B3O3)2(μ-4,4′-bpy) and (Ph3B3O3)2(μ-bpe). J Chem Crystallogr 45, 284–289 (2015). https://doi.org/10.1007/s10870-015-0586-y

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  • DOI: https://doi.org/10.1007/s10870-015-0586-y

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