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Monatshefte für Chemie - Chemical Monthly

, Volume 149, Issue 11, pp 2013–2019 | Cite as

Decarboxylative olefination of potassium benzoates via bimetallic catalysis strategy

  • Mehdi Khalaj
  • Majid Ghazanfarpour-Darjani
  • Saeed Taheri
  • Sajjad Sedaghat
  • Seyed Jalal Hoseyni
Original Paper

Abstract

A novel synthesis of styrene derivatives through decaroxylative olefination of potassium benzoates with alkynes using Pd2dba3/CuBr as catalyst system has been developed. The protocol proceeded smoothly and in most cases Z-alkene was the main product. Electron-rich potassium benzoates reacted more efficiently than those of electron-deficient substrates. Heteroaromatic and electron-deficient aryl alkynes were not consistent with this transformation.

Graphical abstract

Keywords

Bimetallic catalysis Decarboxylation Hydrometalation Benzoic acid Alkyne 

Notes

Acknowledgements

We thank Buinzahra Branch of Islamic Azad University for additional unrestricted support.

Supplementary material

706_2018_2267_MOESM1_ESM.docx (83 kb)
Supplementary material 1 (DOCX 82 kb)

References

  1. 1.
    Liao K, Negretti S, Musaev DG, Bacsa J, Davies HML (2016) Nature 533:230CrossRefPubMedGoogle Scholar
  2. 2.
    Chen W, Ma L, Paul A, Seidel D (2018) Nat Chem 10:165CrossRefPubMedGoogle Scholar
  3. 3.
    Jones WD (2002) Science 295:289CrossRefPubMedGoogle Scholar
  4. 4.
    Seechurn CCCJ, Sperger T, Scrase TG, Schoenebeck F, Colacot TJ (2017) J Am Chem Soc 139:5194CrossRefGoogle Scholar
  5. 5.
    Takise R, Muto K, Yamaguchi J (2017) Chem Soc Rev 46:5864CrossRefPubMedGoogle Scholar
  6. 6.
    Shi S, Szostak M (2017) Chem Commun 53:10584CrossRefGoogle Scholar
  7. 7.
    Myers AG, Tanaka D, Mannion MR (2002) J Am Chem Soc 124:11250CrossRefPubMedGoogle Scholar
  8. 8.
    Hu G, Gao Y, Zhao Y (2014) Org Lett 16:4464CrossRefPubMedGoogle Scholar
  9. 9.
    Kan J, Huang S, Lin J, Zhang M, Su W (2015) Angew Chem Int Ed 54:2199CrossRefGoogle Scholar
  10. 10.
    Sun F, Gu Z (2015) Org Lett 17:2222CrossRefPubMedGoogle Scholar
  11. 11.
    Zhu Y, Li X, Wang X, Huang X, Shen T, Zhang Y, Sun X, Zou M, Song S, Jiao N (2015) Org Lett 17:4702CrossRefPubMedGoogle Scholar
  12. 12.
    Tan H, Li H, Ji W, Wang (2015) Angew Chem Int Ed 54:8374Google Scholar
  13. 13.
    Gooßen LJ, Deng G, Levy LM (2006) Science 313:662CrossRefPubMedGoogle Scholar
  14. 14.
    Gooßen LJ, Lange PP, Rodríguez N, Linder C (2010) Chem Eur J 16:3906CrossRefPubMedGoogle Scholar
  15. 15.
    Rudolphi F, Song B, Gooßen LJ (2011) Adv Synth Catal 353:337CrossRefGoogle Scholar
  16. 16.
    Cahiez G, Moyeux A, Gager A, Poizat M (2013) Adv Synth Catal 355:790CrossRefGoogle Scholar
  17. 17.
    Fang P, Li M, Ge H (2010) J Am Chem Soc 132:11898CrossRefPubMedGoogle Scholar
  18. 18.
    Wen H, Zhang L, Zhu S, Liu G, Huang Z (2017) ACS Catal 7:6419CrossRefGoogle Scholar
  19. 19.
    Traficante CI, Fagundez C, Serra GL, Mata EG, Delpiccolo CML (2016) ACS Comb Sci 18:225CrossRefPubMedGoogle Scholar
  20. 20.
    Kong W, Che C, Wu J, Ma L, Zhu G (2014) J Org Chem 79:5799CrossRefPubMedGoogle Scholar
  21. 21.
    Gordillo A, Ortuño MA, López-Mardomingo C, Lledós A, Ujaque G, de Jesús E (2013) J Am Chem Soc 135:13749CrossRefPubMedGoogle Scholar
  22. 22.
    Ackermann L, Gunnoe TB, Habgood LG (2018) Catalytic hydroarylation of carbon-carbon multiple bonds. Wiley-VCH, WeinheimGoogle Scholar
  23. 23.
    Jia C, Piao D, Oyamada J, Lu W, Kitamura T, Fujiwara Y (2000) Science 287:1992CrossRefPubMedGoogle Scholar
  24. 24.
    Huang L, Biafora A, Zhang G, Bragoni V, Gooßen LJ (2016) Angew Chem Int Ed 55:6933CrossRefGoogle Scholar
  25. 25.
    Zhang X, Li Y, Shi H, Zhang L, Zhang S, Xu X, Liu Q (2014) Chem Commun 50:7306CrossRefGoogle Scholar
  26. 26.
    Manikandan R, Jeganmohan M (2015) Org Biomol Chem 13:10420CrossRefPubMedGoogle Scholar
  27. 27.
    Yamamoto Y (2014) Chem Soc Rev 43:1575CrossRefPubMedGoogle Scholar
  28. 28.
    Shen R, Chen T, Zhao Y, Qiu R, Zhou Y, Yin S, Wang X, Goto M, Han LB (2011) J Am Chem Soc 133:17037CrossRefPubMedGoogle Scholar
  29. 29.
    Jana R, Tunge JA (2011) J Org Chem 76:8376CrossRefPubMedPubMedCentralGoogle Scholar
  30. 30.
    Estes DP, Norton JR, Jockusch S, Sattler W (2012) J Am Chem Soc 134:15512CrossRefPubMedGoogle Scholar
  31. 31.
    Pye DR, Mankad NP (2017) Chem Sci 81:705Google Scholar
  32. 32.
    Mankad NP (2016) Chem Eur J 22:5822CrossRefPubMedGoogle Scholar
  33. 33.
    Vercruysse S, Cornelissen L, Nahra F, Collard L, Riant O (2014) Chem Eur J 20:1834CrossRefPubMedGoogle Scholar
  34. 34.
    Rudolphi F, Song B, Gooßen LJ (2011) Adv Synth Catal 353:337CrossRefGoogle Scholar
  35. 35.
    Cohen T, Berninger RW, Wood JT (1978) J Org Chem 43:837CrossRefGoogle Scholar
  36. 36.
    Cahiez G, Moyeux A, Gager O, Poizat M (2013) Adv Synth Catal 355:790CrossRefGoogle Scholar
  37. 37.
    Gadge ST, Bhanage BM (2013) Synlett 24:981CrossRefGoogle Scholar
  38. 38.
    Giannerini M, Fañanás-Mastral M, Feringa BL (2013) Nat Chem 5:667CrossRefPubMedGoogle Scholar
  39. 39.
    Pérez M, Fañanás-Mastral M, Bos PH, Rudolph A, Harutyunyan SR, Feringa BL (2011) Nat Chem 3:377CrossRefPubMedGoogle Scholar
  40. 40.
    Kondolff I, Doucet H, Santelli M (2003) Tetrahedron Lett 44:8487CrossRefGoogle Scholar
  41. 41.
    Tsuji J, Nogi T (1966) J Am Chem Soc 88:1289CrossRefGoogle Scholar
  42. 42.
    Fructos MR, Díaz-Requejo MM, Pérez PJ (2009) Chem Commun 14:5153CrossRefGoogle Scholar
  43. 43.
    Li J, Liu Q, Shen H, Huang R, Zhang X, Xiong Y, Chen C (2015) RSC Adv 5:85291CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Chemistry, Buinzahra BranchIslamic Azad UniversityBuinzahraIran
  2. 2.Department of Chemistry, Faculty of Science, Shahr-e-Qods BranchIslamic Azad UniversityTehranIran

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