DOI QR코드

DOI QR Code

Palladium-Catalyzed Synthesis of Aryl Ketones from Carboxylic Acids and Arylboronic Acids Using EEDQ

  • Kwon, Young-Bum (Department of Advanced Material Chemistry, Korea University) ;
  • Choi, Bo-Ram (Department of Advanced Material Chemistry, Korea University) ;
  • Lee, Seung-Hwan (Department of Advanced Material Chemistry, Korea University) ;
  • Seo, Jin-Soo (Department of Advanced Material Chemistry, Korea University) ;
  • Yoon, Cheol-Min (Department of Advanced Material Chemistry, Korea University)
  • Received : 2010.05.04
  • Accepted : 2010.07.10
  • Published : 2010.09.20

Abstract

Keywords

References

  1. Dieter, R. K. Tetrahedron 1999, 55, 4177. https://doi.org/10.1016/S0040-4020(99)00184-2
  2. Zhang, Y. D.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 15964. https://doi.org/10.1021/ja044113k
  3. Hatano, B.; Kadokawa, J. I.; Tagaya, H. Tetrahedron Lett. 2002, 43, 5859. https://doi.org/10.1016/S0040-4039(02)01163-2
  4. Shi, M.; Wu, L.; Lu, J.-M. Tetrahedron 2008, 64, 3315. https://doi.org/10.1016/j.tet.2008.02.003
  5. Gmouh, S.; Yang, H.; Vaultier, M. Org. Lett. 2003, 5, 2219. https://doi.org/10.1021/ol034529n
  6. Fillion, E.; Fishlock, D.; Wilsily, A.; Goll, J. M. J. Org. Chem. 2005, 70, 1316. https://doi.org/10.1021/jo0483724
  7. Ruan, J.; Saidi, O.; Iggo, J. A.; Xiao, J. J. Am. Chem. Soc. 2008, 130, 10510. https://doi.org/10.1021/ja804351z
  8. Labadie, J. W.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 669. https://doi.org/10.1021/ja00341a083
  9. Arisawa, M.; Torisawa, Y.; Kawahara, M.; Yamanaka, M.; Nishida, A.; Nakagawa, M. J. Org. Chem. 1997, 62, 4327. https://doi.org/10.1021/jo970244a
  10. Wang, X.-J.; Zhang, L.; Sun, X.; Xu, Y.; Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2005, 7, 5593. https://doi.org/10.1021/ol052150q
  11. Wang, D. H.; Zhang, Z. Z. Org. Lett. 2003, 5, 4645. https://doi.org/10.1021/ol035801w
  12. Haddach, M.; McCarthy, J. R. Tetrahedron Lett. 1999, 40, 3109. https://doi.org/10.1016/S0040-4039(99)00476-1
  13. Urawa, Y.; Ogura, K. Tetrahedron Lett. 2003, 44, 271. https://doi.org/10.1016/S0040-4039(02)02501-7
  14. Bandgar, B. P.; Patil, A. V. Tetrahedron Lett. 2005, 46, 7627. https://doi.org/10.1016/j.tetlet.2005.08.111
  15. Chen, H.; Deng, M. Z. Org. Lett. 2000, 2, 1649. https://doi.org/10.1021/ol000013h
  16. Bumagin, N. A.; Korolev, D. N. Tetrahedron Lett. 1999, 40, 3057. https://doi.org/10.1016/S0040-4039(99)00364-0
  17. Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260. https://doi.org/10.1021/ja005613q
  18. Yu, Y.; Liebeskind, L. S. J. Org. Chem. 2004, 69, 3554. https://doi.org/10.1021/jo049964p
  19. Tatamidani, H.; Kakiuchi, F.; Chatani, N. Org. Lett. 2004, 6, 3597. https://doi.org/10.1021/ol048513o
  20. Xin, B.; Zhang, Y.; Cheng, K. Synthesis 2007, 1970.
  21. Xin, B.; Zhang, Y.; Cheng, K. J. Org. Chem. 2006, 71, 5725. https://doi.org/10.1021/jo060749d
  22. GooBen, L. J.; Ghosh, K. Eur. J. Org. Chem. 2002, 19, 3254.
  23. GooBen, L. J.; Ghosh, K. Chem. Commun. 2001, 2084.
  24. GooBen, L. J.; Winkel, L.; Dohring, A.; Ghosh, K.; Paetzold, J. Synlett 2002, 1237.
  25. GooBen, L. J.; Ghosh, K. Angew. Chem. Int. Ed. 2001, 40, 3458. https://doi.org/10.1002/1521-3773(20010917)40:18<3458::AID-ANIE3458>3.0.CO;2-0
  26. Belleau, B.; Malek, G. J. Am. Chem. Soc. 1968, 90, 1651. https://doi.org/10.1021/ja01008a045
  27. Belleau, B.; Martel, R. R.; Lacasse, G.; Menard, M.; Weinberg, N. L.; Perron, Y. G. J. Am. Chem. Soc. 1968, 90, 823. https://doi.org/10.1021/ja01005a067
  28. Brown, J.; Williams, R. E. Can. J. Chem. 1971, 49, 3765. https://doi.org/10.1139/v71-628
  29. Hyun, M. H.; Kang, M. H.; Han, S. C. Tetrahedron Lett. 1999, 40, 3435. https://doi.org/10.1016/S0040-4039(99)00509-2
  30. Lee, J. H.; Kweon, J. S.; Yoon, C. M. Tetrahedron Lett. 2002, 43, 5771. https://doi.org/10.1016/S0040-4039(02)01184-X
  31. Chang, Y. M.; Lee, S. H.; Nam, M. H.; Cho, M. Y.; Park, Y. S.; Yoon, C. M. Tetrahedron Lett. 2005, 46, 3053. https://doi.org/10.1016/j.tetlet.2005.03.008
  32. Yamaoka, Y.; Miyabe, H.; Takemoto, Y. J. Am. Chem. Soc. 2007, 129, 6686. https://doi.org/10.1021/ja071470x
  33. Kakino, R.; Narahashi, H.; Shimizu, I.; Yamamoto, A. Chem. Lett. 2001, 1242.
  34. Kakino, R.; Narahashi, H.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2002, 75, 137. https://doi.org/10.1246/bcsj.75.137
  35. Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314. https://doi.org/10.1021/ar980063a

Cited by

  1. ChemInform Abstract: Palladium-Catalyzed Synthesis of Aryl Ketones from Carboxylic Acids and Arylboronic Acids Using EEDQ. vol.42, pp.6, 2011, https://doi.org/10.1002/chin.201106104
  2. Acylative Suzuki coupling of amides: acyl-nitrogen activation via synergy of independently modifiable activating groups vol.51, pp.24, 2015, https://doi.org/10.1039/C5CC00430F
  3. Eco-friendly Suzuki–Miyaura coupling of arylboronic acids to aromatic ketones catalyzed by the oxime-palladacycle in biosolvent 2-MeTHF vol.40, pp.4, 2016, https://doi.org/10.1039/C5NJ02734A
  4. Polystyrene-supported Pd(II)-N-heterocyclic carbene complex as a heterogeneous and recyclable precatalyst for cross-coupling of acyl chlorides with arylboronic acids pp.02682605, 2017, https://doi.org/10.1002/aoc.3982
  5. )-one and acridone scaffolds vol.32, pp.3, 2017, https://doi.org/10.1002/aoc.4173
  6. Recent Advances in Acyl Suzuki Cross-Coupling vol.9, pp.1, 2019, https://doi.org/10.3390/catal9010053
  7. Synthesis of Diaryl Ketones through Oxidative Cleavage of the C-C Double Bonds in N-Sulfonyl Enamides vol.83, pp.7, 2018, https://doi.org/10.1021/acs.joc.7b03068
  8. Heteroleptic Palladium(II) Complexes of Thiazolinyl‐picolinamide Derived N N N Pincer Ligand: An Efficient Catalyst for Acylative Suzuki Coupling Reactions vol.10, pp.11, 2021, https://doi.org/10.1002/ajoc.202100490