Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Decarboxylative Heck Reaction of Aryl Iodide with Baylis-Hillman Adduct Using Pd/C as a Catalyst in Aqueous Media

  • Kim, Hyun-Soo (Department of Advanced Material Chemistry, Korea University) ;
  • Lee, Sang-Jin (Department of Advanced Material Chemistry, Korea University) ;
  • Yoon, Cheol Min (Department of Advanced Material Chemistry, Korea University)
  • Received : 2012.08.01
  • Accepted : 2012.10.26
  • Published : 2013.01.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Franck, H. G.; Stadelhofer, J. W. Industrial Aromatic Chemistry; Springer-Verlag: Berlin, 1988.
  2. Surburg, H.; Panten, J. Common Fragrance and Flavor Materials, 5th Ed.; Wiley-VCH: Weinheim, Germany, 2006.
  3. Olah, G. A. Friedel-Crafts Chemistry; Wiley: New York, 1973.
  4. Park, Y. J.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222. https://doi.org/10.1021/ar700133y
  5. Willis, M. C. Chem. Rev. 2010, 110, 725. https://doi.org/10.1021/cr900096x
  6. Takemiya, A.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 14800. https://doi.org/10.1021/ja064782t
  7. A catalytic system of Pyrrolidine, dppp and Pd(dba)2: Ruan, J.; Saidi, O.; Iggo, J. A.; Xiao, J. J. Am. Chem. Soc. 2008, 130, 10510. https://doi.org/10.1021/ja804351z
  8. Zanardi, A.; Mata, J. A.; Peris, E. Organometallics 2009, 28, 1480. https://doi.org/10.1021/om8010504
  9. A in situ generated palladium nanoparticles: Adak, L.; Bhadra, S.; Ranu, B. C. Tetrahedron Lett. 2010, 51, 3811. https://doi.org/10.1016/j.tetlet.2010.05.067
  10. Colbon, P.; Ruan, J.; Purdie, M.; Xiao, J. Org. Lett. 2010, 12, 3670. https://doi.org/10.1021/ol101466g
  11. Sugiura, M.; Sato, N.; Kotani, S.; Nakajima, M. Chem. Commun. 2008, 4309.
  12. Sugiura, M.; Sato, N.; Sonoda, Y.; Kotani, S.; Nakajima, M. Chem. Asian J. 2010, 5, 478. https://doi.org/10.1002/asia.200900450
  13. Kotani, S.; Osakama, K.; Sugiura, M.; Nakajima, M. Org. Lett. 2011, 13, 3968. https://doi.org/10.1021/ol2014895
  14. Basavaiah, D.; Rao, A. J.; Satyanarayama, T. Chem. Rev. 2003, 103, 811. https://doi.org/10.1021/cr010043d
  15. Basavaiah, D.; Veeraraghavaiah, G. Chem. Soc. Rev. 2012, 41, 68. https://doi.org/10.1039/c1cs15174f
  16. Basavaiah, D.; Sekhara Reddy, B.; Singh Badsara, S. Chem. Rev. 2010, 110, 5447. https://doi.org/10.1021/cr900291g
  17. Fu, G. C. Acc. Chem. Res. 2008, 41, 1555. https://doi.org/10.1021/ar800148f
  18. Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174. https://doi.org/10.1021/cr0509760
  19. Brase, S.; deMeijere, A. Cross-Coupling of Organyl Halides with Alkenes: The Heck Reaction. In Metal-Catalyzed Cross- Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley- VCH: New York, NY, 2004, Chapter 5.
  20. Brase, S.; de Meijere, A. The Heck Reaction and Related Carbopalladation Reactions. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; Wiley Interscience: New York, NY, 2002, Chapter IV.2.
  21. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009. https://doi.org/10.1021/cr9903048
  22. Anastas, P. A.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998.
  23. Sheldon, R. A.; Arends, I.; Hanefeld, U. Green Chemistry and Catalysis; Wiley-VCH: Weinheim, 2007.
  24. Blaser, H. U.; Baiker, A.; Prins, R. Heterogeneous Catalysis and Fine Chemicals IV; Elsevier: Netherlands, 1997.
  25. Seki, M. Synthesis 2006, 2975.
  26. Yin, L.; Liebscher, J. Chem. Rev. 2007, 107, 133. https://doi.org/10.1021/cr0505674
  27. Duplais, C.; Forman, A. J.; Baker, B. A.; Lipshutz, B. H. Chem. Eur. J. 2010, 16, 3366. https://doi.org/10.1002/chem.200902471
  28. Kchler, K.; Heidenreich, R. G.; Krauter, J. G. E.; Pietsch, J. Chem. Eur. J. 2002, 8, 622. https://doi.org/10.1002/1521-3765(20020201)8:3<622::AID-CHEM622>3.0.CO;2-0
  29. Lautens, M.; Tayama, E.; Herse, C. J. Am. Chem. Soc. 2005, 127, 72. https://doi.org/10.1021/ja043898r
  30. Felpin, F.-X.; Fouquet, E.; Zakri, C. Adv. Synth. Catal. 2008, 350, 2559. https://doi.org/10.1002/adsc.200800539
  31. Felpin, F.-X.; Ibarguren, O.; Nassar-Hardy, L.; Fouquet, E. J. Org. Chem. 2009, 73, 1349.
  32. Park, J.; Kwon, Y. B.; Yang, K.; Rhee, H.; Yoon, C. M. Synthesis 2010, 661.
  33. Park, Y. S.; Cho, M. Y.; Kwon, Y. B.; Yoo, B. W.; Yoon, C. M. Synth. Commun. 2007, 37, 2677. https://doi.org/10.1080/00397910701465370
  34. Park, J.; Heo, R.; Kim, J.-Y.; Yoo, B. W.; Yoon, C. M. Bull. Korean Chem. Soc. 2009, 30, 1195. https://doi.org/10.5012/bkcs.2009.30.5.1195

Cited by

  1. ChemInform Abstract: Decarboxylative Heck Reaction of Aryl Iodide with Baylis-Hillman Adduct Using Pd/C as a Catalytic in Aqueous Media. vol.44, pp.40, 2013, https://doi.org/10.1002/chin.201340065
  2. Palladium-Catalyzed Desulfitative Oxidative Coupling between Arenesulfinic Acid Salts and Allylic Alcohols: A Strategy for the Selective Construction of β-Aryl Ketones and Aldehydes vol.80, pp.17, 2015, https://doi.org/10.1021/acs.joc.5b01463
  3. Development of the Applications of Palladium on Charcoal in Organic Synthesis vol.360, pp.18, 2018, https://doi.org/10.1002/adsc.201800343
  4. A Highly Active Nickel-Fibre Complex as a Catalyst for the Heck Reaction vol.40, pp.3, 2016, https://doi.org/10.3184/174751916x14547740527373
  5. Palladium Catalyzed Annulation of Morita‐Baylis‐Hillman Adducts: Synthesis of Indene and Indanone Derivatives vol.5, pp.5, 2020, https://doi.org/10.1002/slct.201903515