Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Solvent-free Microwave-Assisted Ortho-Alkylation of Aromatic Ketimine with Acrylic Acid Derivatives by Rh(I) Catalyst

  • Jo, Eun-Ae (Department of Chemistry and Center for Bioactive Molecular Hybrid, Yonsei University) ;
  • Ahn, Jeong-Ae (Department of Chemistry and Center for Bioactive Molecular Hybrid, Yonsei University) ;
  • Jun, Chul-Ho (Department of Chemistry and Center for Bioactive Molecular Hybrid, Yonsei University)
  • Published : 2007.11.20
Download PDF
⟨ Previous Next ⟩

Abstract

The article reports the synthesis of a novel bispyridino-18-crown-6 ether, 7-{[(5S,15S)-5,15-diphenyl- 3,6,14,17-tetraoxa-23,24-diazatricyclo[17.3.1.18,12]tetracosa-1(23),8(24),9,11,19,21-hexaen-10-yl]oxy}heptylferrocenamide 6, bearing the C2-symmetric diphenyl substituents as chiral barriers and the ferrocenyl groups serving as an electrochemical sensor, and its electrochemical study with D- and L-AlaOMe·HCl as the guest by cyclovoltametry.

Keywords

References

  1. Dyker, G. In Handbook of C-H Transformations; Wiley-VCH: Weinheim (Germany), 2005
  2. Kakiuchi, F.; Chatani, N. Adv. Synth. Catal. 2003, 345, 1077-1101 https://doi.org/10.1002/adsc.200303094
  3. Ritleng, V.; Sirlins, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1769 https://doi.org/10.1021/cr0104330
  4. Dyker, G. Angew. Chem. Int. Ed. 1999, 38, 1698-1712 https://doi.org/10.1002/(SICI)1521-3773(19990614)38:12<1698::AID-ANIE1698>3.0.CO;2-6
  5. Park, Y.-J.; Jun, C.-H. Bull. Korean Chem. Soc. 2005, 26, 871-877 https://doi.org/10.5012/bkcs.2005.26.6.871
  6. Cho, C.-S.; Kim, D.-Y.; Shim, S.-C. Bull. Korean Chem. Soc. 2005, 26, 802-804 https://doi.org/10.5012/bkcs.2005.26.5.802
  7. Kakiuchi, F.; Murai, S. In Activation of Unreactive Bonds and Organic Synthesis; Murai, S., Ed.; Springer: Berlin, German, 1999
  8. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529-530 https://doi.org/10.1038/366529a0
  9. Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62 https://doi.org/10.1246/bcsj.68.62
  10. Murai, S.; Chatani, N.; Kakiuchi, F. Pure Appl. Chem. 1997, 69, 589-594 https://doi.org/10.1351/pac199769030589
  11. Sonoda, M.; Kakiuchi, F.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1997, 70, 3117 https://doi.org/10.1246/bcsj.70.3117
  12. Sonoda, M.; Kakiuchi, F.; Kamatani, A.; Chatani, N.; Murai, S. Chem. Lett. 1996, 109-110
  13. Kakiuchi, F.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1996, 111-112
  14. Jun, C.-H.; Moon, C. W.; Hong, J.-B.; Lim, S.-G.; Chung, K.-Y.; Kim, Y.-H. Chem. Eur. J. 2002, 8, 485-492 https://doi.org/10.1002/1521-3765(20020118)8:2<485::AID-CHEM485>3.0.CO;2-1
  15. Jun, C.-H.; Hong, J.-B.; Kim, Y.-H.; Chung, K.-Y. Angew. Chem., Int. Ed. 2000, 39, 3440-3442 https://doi.org/10.1002/1521-3773(20001002)39:19<3440::AID-ANIE3440>3.0.CO;2-1
  16. Lim, S.-G.; Lee, J. H.; Moon, C. W.; Hong, J. B.; Jun, C.-H. Org. Lett. 2003, 5, 2759-2761 https://doi.org/10.1021/ol035083d
  17. Lim, S.-G.; Ahn, J.-A.; Jun, C.-H. Org. Lett. 2004, 6, 4687-4690 https://doi.org/10.1021/ol048095n
  18. Loupy, A. In Microwaves in Organic Synthesis, 2nd ed.; Wiley-VCH: Weinheim (Germany), 2006
  19. Kappe, C. O.; Stadler, A. In Microwaves in Organic and Medicinal Chemistry; Wiley-VCH: 2005
  20. Kim, Y.-H.; Kim, Y.-J.; Chang, S.-Y.; Kim, B.-T.; Heo, J.-N. Bull. Korean Chem. Soc. 2007, 28, 777-782 https://doi.org/10.5012/bkcs.2007.28.5.777
  21. Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223 https://doi.org/10.1016/S0040-4020(01)00905-X
  22. Loupy, A. In Microwaves in Organic Synthesis, 2nd ed.; Wiley-VCH: Weinheim (Germany), 2006, p 134-218
  23. Ahn, J.-A.; Chang, D.-H.; Park, Y. J.; Yon, Y. R.; Loupy, A.; Jun, C.-H. Adv. Synth. Catal. 2006, 348, 55-58 https://doi.org/10.1002/adsc.200505233
  24. Loupy, A.; Chatti, S.; Delamare, S.; Lee, D.-Y.; Chung, J.-H.; Jun, C.-H. J. Chem. Soc., Perkin Trans. 1 2002, 10, 1280-1285
  25. Jun, C.-H.; Chung, J.-H.; Lee, D.-Y.; Loupy, A.; Chatti, S. Tetrahedron Lett. 2001, 42, 4803-4805 https://doi.org/10.1016/S0040-4039(01)00853-X
  26. Osborn, J. A.; Wilkinson, G. In Reagents for Transition Metal Complex and Organometallic Syntheses; Angelici, R., Ed.; Wiley: New York, 1989; Vol. 28, pp 77-79
  27. Thalji, R. K.; Ellman, J. A.; Bergman, R. G. J. Am. Chem. Soc. 2004, 126, 7192-7193 https://doi.org/10.1021/ja0394986

Cited by

  1. ChemInform Abstract: Solvent-Free Microwave-Assisted ortho-Alkylation of Aromatic Ketimine with Acrylic Acid Derivatives by Rh(I) Catalyst. vol.39, pp.12, 2008, https://doi.org/10.1002/chin.200812037
  2. Synthesis of Phloroglucinol Using Microwave-Assisted Reaction from TNT vol.30, pp.12, 2007, https://doi.org/10.5012/bkcs.2009.30.12.3105
  3. Solvent-free Cleavage of tert-Butyl Esters under Microwave Conditions vol.30, pp.1, 2007, https://doi.org/10.5012/bkcs.2009.30.1.230
  4. Rhodium-Catalyzed C−C Bond Formation via Heteroatom-Directed C−H Bond Activation vol.110, pp.2, 2007, https://doi.org/10.1021/cr900005n
  5. Solvent-Free Michael Addition Between EMME and Secondary Amine under Focused Microwave Irradiation vol.31, pp.5, 2007, https://doi.org/10.5012/bkcs.2010.31.5.1155
  6. Regiospecific synthesis of functionalised 1,3-diarylisobenzofurans via palladium- and rhodium-catalysed reaction of boronic acids with o-acylbenzaldehydes under thermal or microwave activation vol.8, pp.21, 2010, https://doi.org/10.1039/c0ob00110d
  7. Ru‐Catalyzed Branched versus Linear Selective C3‐Alkylation of 2‐Aroylbenzofurans with Acrylates via CH Activation vol.20, pp.26, 2007, https://doi.org/10.1002/chem.201400401