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Synthesis of Vinylsulfones Via Palladium-Catalyzed Decarboxylative Coupling of Cinnamic Acids with Aromatic Sulfinic Acid Sodium Salts

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Abstract

A highly efficient synthesis of vinylsulfones was achieved via decarboxylative cross-coupling reaction of cinnamic acids with aromatic sulfinic acid sodium salts catalyzed by Pd(OAc)2 and dppb in the presence of Ag2CO3. The reaction was found to furnish various vinylsulfones in good yields instead of the expected desulfitative product stilbenes. Mechanistic investigation also suggested that the decarboxylation is likely to take place after the transmetallation step.

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References

  1. Goossen LJ, Rodriguez N, Goossen K (2008) Angew Chem Int Ed 120:3100

    Article  Google Scholar 

  2. Goossen LJ, Collet F, Goossen K (2010) Isr J Chem 50:617

    Article  CAS  Google Scholar 

  3. Rodriguez N, Goossen LJ (2011) Chem Soc Rev 40:5030

    Article  CAS  Google Scholar 

  4. Nilsson M (1996) Acta Chem Scand 20:423

    Article  Google Scholar 

  5. Goossen LJ, Paetzold J, Winkel L (2002) Synlett 10:1721

    Article  Google Scholar 

  6. Goossen LJ, Paetzold J (2002) Angew Chem Int Ed 41:1237

    Article  CAS  Google Scholar 

  7. Goossen LJ, Paetzold J (2004) Adv Synth Catal 346:1665

    Article  CAS  Google Scholar 

  8. Goossen LJ, Paetzold J (2004) Chem Int Ed 43:1095

    Article  CAS  Google Scholar 

  9. Goossen LJ, Deng G, Levy LM (2006) Science 313:662

    Article  CAS  Google Scholar 

  10. Goossen LJ, Rodriguez N, Melzer B, Linder C, Deng G, Levy LM (2007) J Am Chem Soc 129:4824

    Article  CAS  Google Scholar 

  11. Goossen LJ, Linder C, Rodriguez N, Lange PP (2009) Chem Eur J 15:9336

    Article  CAS  Google Scholar 

  12. Myers AG, Tanaka D, Mannion MR (2002) J Am Chem Soc 124:11250

    Article  CAS  Google Scholar 

  13. Tanaka D, Myers AG (2004) Org Lett 6:433

    Article  CAS  Google Scholar 

  14. Tanaka D, Romeril SP, Myers AG (2005) J Am Chem Soc 127:10323

    Article  CAS  Google Scholar 

  15. Hu P, Kan J, Su W, Hong M (2009) Org Lett 11:2341

    Article  CAS  Google Scholar 

  16. Zhang S, Fu Y, Shang R, Guo Q, Liu L (2010) J Am Chem Soc 132:638

    Article  CAS  Google Scholar 

  17. Wang Z, Ding Q, He X, Wu J (2009) Org Biomol Chem 7:863

    Article  CAS  Google Scholar 

  18. Becht JM, Catala C, Drian CL, Wagner A (2007) Org Lett 9:1781

    Article  CAS  Google Scholar 

  19. Voutchkova A, Coplin A, Leadbeater NE, Crabtree RH (2008) Chem Commun 47:6312

    Article  Google Scholar 

  20. Becht JM, Drian CL (2008) Org Lett 10:3161

    Article  CAS  Google Scholar 

  21. Shang R, Xu Q, Jiang Y, Wang Y, Liu L (2010) Org Lett 12:1000

    Article  CAS  Google Scholar 

  22. Forgione P, Brochu MC, St-Onge M, Thesen KH, Bailey MD, Bilodeau F (2006) J Am Chem Soc 128:11350

    Article  CAS  Google Scholar 

  23. Baudoin O (2007) Angew Chem Int Ed 46:1373

    Article  CAS  Google Scholar 

  24. Cornella J, Lu P, Larrosa I (2009) Org Lett 11:5506

    Article  CAS  Google Scholar 

  25. Zhou J, Hu P, Zhang M, Huang S, Wang M, Su W (2010) Chem Eur J 16:5876

    Article  CAS  Google Scholar 

  26. Hu P, Zhang M, Jie X, Su W (2012) Angew Chem Int Ed 51:227

    Article  CAS  Google Scholar 

  27. Xie K, Yang Z, Zhou X, Li X, Wang S, Tan Z, An X, Guo CC (2010) Org Lett 12:1564

    Article  CAS  Google Scholar 

  28. Zhang F, Greaney MF (2010) Angew Chem Int Ed 49:2768

    Article  CAS  Google Scholar 

  29. Zhao H, Wei Y, Xu J, Kan J, Su W, Hong M (2011) J Org Chem 76:882

    Article  CAS  Google Scholar 

  30. Cornella J, Lahlali H, Larrosa I (2010) Chem Commun 46:8276

    Article  CAS  Google Scholar 

  31. Xie K, Wang S, Yang Z, Liu J, Wang A, Li X, Tan Z, Guo CC, Deng W (2011) Eur J Org Chem 17:5787

    Article  Google Scholar 

  32. Hu P, Shang YP, Su W (2012) Angew Chem Int Ed 51:5945

    Article  CAS  Google Scholar 

  33. Goossen LJ, Rudolphi F, Oppel C, Rodriguez N (2008) Angew Chem Int Ed 47:3043

    Article  CAS  Google Scholar 

  34. Fang P, Li M, Ge H (2010) J Am Chem Soc 132:11898

    Article  CAS  Google Scholar 

  35. Li M, Ge H (2010) Org Lett 12:3464

    Article  CAS  Google Scholar 

  36. Rodriguez N, Manjolinhao F, Grunberg MF, Goossen LJ (2011) Chem Eur J 17:13688

    Article  CAS  Google Scholar 

  37. Li M, Wang C, Ge H (2011) Org Lett 13:2062

    Article  CAS  Google Scholar 

  38. Wang H, Guo LN, Duan XH (2012) Org Lett 14:4358

    Article  CAS  Google Scholar 

  39. Shang R, Fu Y, Li J, Zhang S, Guo Q, Liu L (2009) J Am Chem Soc 131:5738

    Article  CAS  Google Scholar 

  40. Shang R, Sheng D, Chu L, Fu Y, Liu L (2011) Angew Chem Int Ed 123:4562

    Article  Google Scholar 

  41. Shang R, Yang Z, Wang Y, Zhang S, Liu L (2010) J Am Chem Soc 132:14391

    Article  CAS  Google Scholar 

  42. Shang R, Huang Z, Chu L, Fu Y, Liu L (2011) Org Lett 13:4240

    Article  CAS  Google Scholar 

  43. Wang C, Rakshit S, Glorius F (2010) J Am Chem Soc 132:14006

    Article  CAS  Google Scholar 

  44. Wang C, Piel I, Glorius F (2009) J Am Chem Soc 131:4194

    Article  CAS  Google Scholar 

  45. Adams CM, Ghosh I, Kishi Y (2004) Org Lett 6:4723

    Article  CAS  Google Scholar 

  46. Trost BM, Shen HC, Surivet JP (2004) J Am Chem Soc 126:12565

    Article  CAS  Google Scholar 

  47. Wang Q, Sasaki NA (2004) J Org Chem 69:4767

    Article  CAS  Google Scholar 

  48. Xiao F, Chen H, Xie H, Chen S, Luo Y, Deng GJ (2014) Org. Lett 16:50

    Article  CAS  Google Scholar 

  49. Graves K (1970) J Org Chem 35:3273

    Article  Google Scholar 

  50. Sato K, Okoshi T (1992) Patent US 5159082

  51. Wang M, Li DK, Zhou W, Wang L (2012) Tetrahedron 68:1926

    Article  CAS  Google Scholar 

  52. Wu M, Luo J, Xiao F, Zhang S, Deng GJ, Luo HA (2012) Adv Synth Catal 354:335

    Article  CAS  Google Scholar 

  53. Yang FL, Ma XT, Tian SK (2012) Chem Eur J 18:1582

    Article  CAS  Google Scholar 

  54. Rao H, Yang L, Shuai Q, Li CJ (2011) Adv Synth Catal 353:1701

    Article  CAS  Google Scholar 

  55. Zhao F, Luo J, Tan Q, Liao Y, Peng S, Deng GJ (2012) Adv Synth Catal 354:1914

    Article  CAS  Google Scholar 

  56. Liu J, Zhou X, Rao H, Xiao F, Li CJ, Deng GJ (2011) Chem Eur J 17:7996

    Article  CAS  Google Scholar 

  57. Liu B, Guo Q, Cheng Y, Lan J, You J (2011) Chem Eur J 17:13415

    Article  CAS  Google Scholar 

  58. Chen J, Sun Y, Liu B, Liu D, Cheng J (2012) Chem Commun 48:449

    Article  CAS  Google Scholar 

  59. Yu X, Li X, Wan B (2012) Org Biomol Chem 10:7479

    Article  CAS  Google Scholar 

  60. Wang H, Li Y, Zhang R, Jin K, Zhao D, Duan C (2012) J Org Chem 77:4849

    Article  CAS  Google Scholar 

  61. Zhou C, Liu Q, Li Y, Zhang R, Fu X, Duan C (2012) J Org Chem 77:10468

    Article  CAS  Google Scholar 

  62. Zhou X, Luo J, Liu J, Peng S, Deng GJ (2011) Org Lett 13:6

    Google Scholar 

  63. Biswanath D, Maram L, Kongara D, Nisith B (2011) Synthesis 18:2941

    Google Scholar 

  64. Nobukazu T (2011) Synlett 9:1308

    Google Scholar 

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Acknowledgments

We thank the financial support of National Natural Science Foundation of China (Grants J1210040, J1103312).

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Hunan University, Changsha, 410082, People’s Republic of China

    Ruqing Guo, Qingwen Gui, Dadian Wang & Ze Tan

Authors
  1. Ruqing Guo
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  2. Qingwen Gui
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  3. Dadian Wang
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  4. Ze Tan
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Corresponding author

Correspondence to Ze Tan.

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Guo, R., Gui, Q., Wang, D. et al. Synthesis of Vinylsulfones Via Palladium-Catalyzed Decarboxylative Coupling of Cinnamic Acids with Aromatic Sulfinic Acid Sodium Salts. Catal Lett 144, 1377–1383 (2014). https://doi.org/10.1007/s10562-014-1286-5

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  • DOI: https://doi.org/10.1007/s10562-014-1286-5

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