Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A Highly Efficient and Inexpensive Palladium-Salen Complex for Room Temperature Suzuki-Miyaura Reaction

  • Received : 2014.01.06
  • Accepted : 2014.02.17
  • Published : 2014.06.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. (a) Catellani, M.; Motti, E.; Della Ca', N.; Ferraccioli, R. Eur. J. Org. Chem. 2007, 4153.
  2. (b) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174. https://doi.org/10.1021/cr0509760
  3. (c) Suzuki, A. Angew. Chem., Int. Ed. 2011, 50, 6722. https://doi.org/10.1002/anie.201101379
  4. (d) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. https://doi.org/10.1021/cr00039a007
  5. (e) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359. https://doi.org/10.1021/cr000664r
  6. (f) Suzuki, A. In Boronic Acids. Preparation, Applications in Organic Synthesis and Medicine; Hall, D. G., Ed.; Wiley-VCH: Weinheim, 2005; p 123.
  7. (a) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314. https://doi.org/10.1021/ar980063a
  8. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. https://doi.org/10.1021/cr00039a007
  9. (c) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. 2000, 39, 4153. https://doi.org/10.1002/1521-3773(20001117)39:22<4153::AID-ANIE4153>3.0.CO;2-T
  10. (a) Littke, F. A.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176. https://doi.org/10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U
  11. (b) Guo, M.; Jian, F.; He, R. Tetrahedron Lett. 2005, 46, 9017. https://doi.org/10.1016/j.tetlet.2005.10.104
  12. (c) Dai, W. M.; Zhang, Y. Tetrahedron Lett. 2005, 46, 1377. https://doi.org/10.1016/j.tetlet.2004.12.133
  13. (d) Teo, S.; Weng, Z.; Hor, T. S. A. Organometallics 2006, 25, 1199. https://doi.org/10.1021/om050791j
  14. (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722. https://doi.org/10.1021/ja982250+
  15. (b) Wolf, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413. https://doi.org/10.1002/(SICI)1521-3773(19990816)38:16<2413::AID-ANIE2413>3.0.CO;2-H
  16. (a) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. Angew Chem., Int. Ed. 2002, 41, 4120. https://doi.org/10.1002/1521-3773(20021104)41:21<4120::AID-ANIE4120>3.0.CO;2-7
  17. (b) Huang, R.; Shaughnessy, K. H. Organometallics 2006, 25, 4105. https://doi.org/10.1021/om050940y
  18. (c) Marziale, A. N.; Faul, S. H.; Reiner, T.; Schneider, S.; Eppinger, J. Green Chem. 2010, 12, 35. https://doi.org/10.1039/b915436a
  19. (a) Singh, R.; Viciu, M. S.; Kramareva, N.; Navarro, O.; Nolan, S. P. Org. Lett. 2005, 7, 1829. https://doi.org/10.1021/ol050472o
  20. (b) Marion, N.; Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.; Nolan, S. P. J. Am. Chem. Soc. 2006, 128, 4101. https://doi.org/10.1021/ja057704z
  21. (c) Karimi, B.; Akhavan, P. F. Chem. Commun. 2009, 3750.
  22. (d) Turkmen, H.; Can, R.; Cetinkaya, B. Dalton Trans. 2009, 7039.
  23. (a) Tao, B.; Boykin, D. W. Tetrahedron Lett. 2003, 44, 7993. https://doi.org/10.1016/j.tetlet.2003.08.116
  24. (b) Li, J.-H.; Liu, W.-J. Org. Lett. 2004, 6, 2809. https://doi.org/10.1021/ol048907f
  25. (c) Huang, R.; Shaughnessy, K. H. Organometallics 2006, 25, 4105. https://doi.org/10.1021/om050940y
  26. (d) Chahen, L.; Therrien, B.; Suss-Fink, G. Eur. J. Inorg. Chem. 2007, 32, 5045.
  27. (e) Das, P.; Sarmah, C.; Tairai, A.; Bora, U. Appl. Organomet. Chem. 2011, 25, 283. https://doi.org/10.1002/aoc.1755
  28. (a) Botella, L.; Najera, C. Angew. Chem., Int. Ed. 2002, 41, 179. https://doi.org/10.1002/1521-3773(20020104)41:1<179::AID-ANIE179>3.0.CO;2-O
  29. (b) Rao, G. K.; Kumar, A.; Ahmedz, J.; Singh, A. K. Chem. Commun. 2010, 46, 5954. https://doi.org/10.1039/c0cc01075h
  30. (c) Susanto, W.; Chu, C.-Y.; Ang, W. J.; Chou, T.-C.; Lo, L.-C.; Lam, Y. Green Chem. 2012, 14, 77. https://doi.org/10.1039/c1gc16108c
  31. Costa, D. P.; Nobre, S. M. Tetrahedron Lett. 2013, 54, 4582. https://doi.org/10.1016/j.tetlet.2013.06.110
  32. (a) Suresh, S. R.; Waghmade, S. B. Tetrahedron Lett. 2008, 49, 3423. https://doi.org/10.1016/j.tetlet.2008.03.109
  33. (b) Naeimi, H.; Rabiei, K. J. Chin. Chem. Soc. 2007, 54, 1293. https://doi.org/10.1002/jccs.200700182
  34. (c) Banik, B.; Tairai, A.; Shahnaz, N.; Das, P. Tetrahedron Lett. 2012, 53, 5624. https://doi.org/10.1016/j.tetlet.2012.08.004
  35. (d) Shahnaz, N.; Banik, B.; Das, P. Tetrahedron Lett. 2013, 54, 2886. https://doi.org/10.1016/j.tetlet.2013.03.115
  36. (a) Rao, G. K.; Kumar, A.; Kumar, B.; Kumar, D.; Singh, A. K. Dalton Trans. 2012, 41, 1931. https://doi.org/10.1039/c1dt11695a
  37. (b) Kostas, I. D.; Steele, B. R.; Terzis, A.; Amosova, S. V.; Martynov, A. V.; Makhaeva, N. A. Eur. J. Inorg. Chem. 2006, 2642.
  38. (c) Kylmala, T.; Kuuloja, N.; Xu, Y.; Rissanen, K.; Franzen, R. Eur. J. Org. Chem. 2008, 4019.
  39. (d) Tas, E.; Kilic, A.; Durgun, M.; Yilmaz, I.; Ozdemir, I.; Gurbuz, N. J. Org. Chem. 2009, 446.
  40. Lai, Y.-C.; Chen, H.-Y.; Hung, W.-C.; Lin, C.-C.; Hong, F.-E. Tetrahedron 2005, 61, 9484. https://doi.org/10.1016/j.tet.2005.08.005
  41. (a) Pasini, A.; Ferrari, R. P.; Lanfranconi, S.; Pozzi, A.; Laurenti, E.; Moroni, M. Inorganica Chimica Acta 1997, 266, 1. https://doi.org/10.1016/S0020-1693(97)05730-7
  42. (b) Naeimi, H.; Rabiei, K.; Salimi, F. Bull. Korean Chem. Soc. 2008, 29, 2445. https://doi.org/10.5012/bkcs.2008.29.12.2445
  43. (a) Velusamy, S.; Punniyamurthy, T. Eur. J. Org. Chem. 2003, 3913.
  44. (b) Velusamy, S.; Srinivasan, A.; Punniyamurthy, T. Tetrahedron Lett. 2006, 47, 923. https://doi.org/10.1016/j.tetlet.2005.11.149

Cited by

  1. Pd(II) salen complex covalently anchored to multi-walled carbon nanotubes as a heterogeneous and reusable precatalyst for Mizoroki-Heck and Hiyama cross-coupling reactions vol.29, pp.1, 2014, https://doi.org/10.1002/aoc.3246
  2. ChemInform Abstract: A Highly Efficient and Inexpensive Palladium-Salen Complex for Room Temperature Suzuki-Miyaura Reaction. vol.45, pp.52, 2014, https://doi.org/10.1002/chin.201452093
  3. Magnetic nanoparticle-tethered Schiff base-palladium(II): Highly active and reusable heterogeneous catalyst for Suzuki-Miyaura cross-coupling and reduction of nitroarenes in aqueous medium at room temperature vol.32, pp.4, 2018, https://doi.org/10.1002/aoc.4266
  4. NC Palladacycles and C,C-chelating phosphorus ylide complexes: synthesis, X-ray characterization, and comparison of the catalytic activity in the Suzuki-Miyaura reaction vol.69, pp.5, 2016, https://doi.org/10.1080/00958972.2016.1151876
  5. Organic Solvent-Free, Pd(II)-Salan Complex-Catalyzed Synthesis of Biaryls via Suzuki-Miyaura Cross-Coupling in Water and Air vol.83, pp.24, 2014, https://doi.org/10.1021/acs.joc.8b02340
  6. Palladium (II)–Salan Complexes as Catalysts for Suzuki–Miyaura C–C Cross-Coupling in Water and Air. Effect of the Various Bridging Units within the Diamine Moieties on the Catalyt vol.25, pp.17, 2014, https://doi.org/10.3390/molecules25173993
  7. An Overview of Solid Supported Palladium and Nickel Catalysts for C-C Cross Coupling Reactions vol.17, pp.5, 2014, https://doi.org/10.2174/1570193x16666190617160339
  8. N, O-polydentate ligands for palladium-catalyzed cross-coupling reactions (Part III) vol.957, pp.None, 2014, https://doi.org/10.1016/j.jorganchem.2021.122147