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A novel self-promoted Morita-Baylis-Hillman-like dimerization

  • Letter
  • Organic Chemistry
  • Published:
Chinese Science Bulletin

Abstract

While stable in CH2Cl2, hexane or THF, in the presence of MeOH, self-promoted dimerization of the triarylphosphine-alkene 1, a ligand for Pd-catalyzed reactions, produced an unusual racemic bis(phosphine) 2 in high yield. The reaction of 2 with Pd(dba)2, followed by oxidative addition of p-IC6H4NO2, yielded a trans-chelated Pd(II) aryl iodide complex.

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References

  1. Morita K, Suzuki Z, Hirose H. Bull Chem Soc Jpn, 1968, 41: 2815

    Article  Google Scholar 

  2. Baylis A B, Hillman M E D. German Patent 2155113 [Chem Abstr 1972, 77, 34174q], 1972

  3. Basavaiah D, Rao P D, Hyma R S. Tetrahedron, 1996, 52: 8001–8062

    Article  Google Scholar 

  4. lmeida W P, Coelho F. Tetrahedron Lett, 2003, 44: 937–940

    Article  Google Scholar 

  5. Feltrin M P, Almeida W P. Synth Commun, 2003, 33: 1141–1146

    Article  Google Scholar 

  6. Iwabuchi Y, Furukawa M, Esumi T, et al. Chem Commun, 2001, 2030–2031

  7. Liu Y, Shi M. Adv Synth Catal, 2008, 350: 122–128

    Article  Google Scholar 

  8. Ciganek E. Organic Reactions, 1997, 51: 201–350

    Google Scholar 

  9. Singh V, Batra S. Tetrahedron, 2008, 64: 4511–4574

    Article  Google Scholar 

  10. Masson G, Housseman C, Zhu J. Angew Chem Int Ed, 2007, 46:4614–4628

    Article  Google Scholar 

  11. Krishna P R, Reddy P V N, Sreeshailam A, et al. Tetrahedron Lett, 2007, 48: 6466–6470

    Article  Google Scholar 

  12. Zhou A, Hanson P R. Org Lett, 2008, 10: 2951–2954

    Article  Google Scholar 

  13. Tang H, Zhao G, Zhou Z, et al. Eur J Org Chem, 2008, 126–135

  14. Jiang Y, Shi Y, Shi M. J Am Chem Soc, 2008, 130: 7202–7203

    Article  Google Scholar 

  15. Cabrera S, Aleman J, Bolze P, et al. Angew Chem Int Ed, 2008, 47: 121–125

    Article  Google Scholar 

  16. Van Steenis D J V C, Marcelli T, Lutz M, et al. Adv Synth Catal, 2007, 349: 281–286

    Article  Google Scholar 

  17. Utsumi N, Zhang H, Tanaka F, et al. Angew Chem Int Ed, 2007, 46: 1878–1880

    Article  Google Scholar 

  18. Trost B M, Brennan M K. Org Lett, 2007, 9: 3961–3964

    Article  Google Scholar 

  19. Langer P. Angew Chem Int Ed, 2000, 39: 3049–3052

    Google Scholar 

  20. Basavaiah D, Rao A J, Satyanarayana T. Chem Rev, 2003, 103: 811–891

    Article  Google Scholar 

  21. Price K E, Broadwater S J, Walker B J, et al. J Org Chem, 2005, 70: 3980–3987

    Article  Google Scholar 

  22. Aggarwal V K, Fulford S Y, Lloyd-Jones G C. Angew Chem Int Ed, 2005, 44: 1706–1708

    Article  Google Scholar 

  23. Kataoka T, Kinoshita H, Iwama T, et al. Tetrahedron, 2000, 56: 4725–4731

    Article  Google Scholar 

  24. Santos L S, Pavam C H, Almeida W P, et al. Angew Chem Int Ed, 2004, 43: 4330–4333

    Article  Google Scholar 

  25. Shi M, Li C, Jiang J. Reexamination of the traditional Baylis-Hillman reaction. Tetrahedron, 2003, 59: 1181–1189

    Article  Google Scholar 

  26. Perlmutter P, Puniani E, Westman G. Tetrahedron Lett, 1996, 37: 1715–1718

    Article  Google Scholar 

  27. Khan A A, Emslie N D, Drewes S E, et al. Chem Ber, 1993, 126: 1477–1480

    Article  Google Scholar 

  28. Auge J, Lubin N, Lubineau A. Tetrahedron Lett, 1994, 35: 7947–7948

    Google Scholar 

  29. Basavaiah D, Krishnamacharyulu M, Rao J. Synth Commun, 2000, 30: 2061–2069

    Article  Google Scholar 

  30. Aggarwal V K, Dean D K, Mereu A, et al. J Org Chem, 2002, 67: 510–514

    Article  Google Scholar 

  31. Yu C, Liu B, Hu L. J Org Chem, 2001, 66: 5413–5418

    Article  Google Scholar 

  32. Cai J, Zhou Z, Zhao G, et al. Org Lett, 2002, 4: 4723–4725

    Article  Google Scholar 

  33. Roy D, Sunoj R B. Org Lett, 2007, 9: 4873–4876

    Article  Google Scholar 

  34. Robiette R, Aggarwal V K, Harvey J N. J Am Chem Soc, 2007, 129: 15513–15525

    Article  Google Scholar 

  35. Jones C E S, Turega S M, Clarke M L, et al. Tetrahedron Lett, 2008, 49: 4666–4669

    Article  Google Scholar 

  36. Balzer M M, Anderson J D. J Org Chem, 1965, 30: 1357–1360

    Article  Google Scholar 

  37. Basavaiah D, Gowriswari V V L, Bharathi T K. Tetrahedron Lett, 1987, 28: 4591–4592

    Article  Google Scholar 

  38. Amri H, Rambaud M, Villieras J. Tetrahedron Lett, 1989, 30: 7381–7382

    Article  Google Scholar 

  39. Hwu J R, Hakimelahi G H, Chou C T. Tetrahedron Lett, 1992, 33: 6469–6472

    Article  Google Scholar 

  40. Jenner G. Tetrahedron Lett, 2000, 41: 3091–3094

    Article  Google Scholar 

  41. Luo X C, Zhang H, Duan H, et al. Org Lett, 2007, 9: 4571–4574

    Article  Google Scholar 

  42. Shi W, Luo Y D, Luo X C, et al. Investigation of an efficient palladium-catalyzed C(sp)-C(sp) cros. J Am Chem Soc, 2008, 130: 14713–14720

    Article  Google Scholar 

  43. Zhang H, Luo X C, Wongkhan K, et al. Chem Eur J, 2009, 15: 3823–3829

    Article  Google Scholar 

  44. Lam KC, Lin Z, Marder T B. Organometallics, 2007, 26: 758–760

    Article  Google Scholar 

  45. Lin B L, Liu L, Fu Y, et al. Comparing nickel- and palladium-catalyzed Heck reactions. Organometallics, 2004, 23: 2114–2123

    Article  Google Scholar 

  46. Li Z, Fu Y, Guo Q X, et al. Organometallics, 2008, 27: 4043–4049

    Article  Google Scholar 

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Author information

Authors and Affiliations

  1. College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China

    Qiang Li, XianCai Luo & AiWen Lei

  2. Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, UK

    Qiang Li, Kittiya Wongkhan, Andrei S. Batsanov, Judith A. K. Howard & Todd B. Marder

  3. College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, China

    Yu Lan & YunDong Wu

Authors
  1. Qiang Li
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  2. Kittiya Wongkhan
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  3. XianCai Luo
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  4. Andrei S. Batsanov
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  5. Judith A. K. Howard
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  6. Yu Lan
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  7. YunDong Wu
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  8. Todd B. Marder
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  9. AiWen Lei
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Corresponding authors

Correspondence to YunDong Wu, Todd B. Marder or AiWen Lei.

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Li, Q., Wongkhan, K., Luo, X. et al. A novel self-promoted Morita-Baylis-Hillman-like dimerization. Chin. Sci. Bull. 55, 2794–2798 (2010). https://doi.org/10.1007/s11434-010-3270-9

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  • DOI: https://doi.org/10.1007/s11434-010-3270-9

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