Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

AuCl3-Catalyzed Propargylation of Arenes with N-Tosylpropargyl Amine: Synthesis of 1,3-Diarylpropynes

  • Lee, Ka-Young (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Lee, Hyun-Seung (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Hoo-Sook (Department of Chemistry and Institute of Basic Science, Chonnam National University) ;
  • Kim, Jae-Nyoung (Department of Chemistry and Institute of Basic Science, Chonnam National University)
  • Published : 2008.08.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Kennedy-Smith, J. J.; Young, L. A.; Toste, F. D. Org. Lett. 2004, 6, 1325-1327 https://doi.org/10.1021/ol049649p
  2. Nishibayashi, Y.; Inada, Y.; Yoshikawa, M.; Hidai, M.; Uemura, S. Angew. Chem. Int. Ed. 2003, 42, 1495- 1498 https://doi.org/10.1002/anie.200250532
  3. Georgy, M.; Boucard, V.; Campagne, J.-M. J. Am. Chem. Soc. 2005, 127, 14180-14181 https://doi.org/10.1021/ja0534147
  4. Liu, J.; Muth, E.; Florke, U.; Henkel, G.; Merz, K.; Sauvageau, J.; Schwake, E.; Dyker, G. Adv. Synth. Catal. 2006, 348, 456-462 https://doi.org/10.1002/adsc.200505411
  5. Zhan, Z.-p.; Yu, J.-l.; Liu, H.-j.; Cui, Y.-y.; Yang, R.-f.; Yang, W.-z.; Li, J.-p. J. Org. Chem. 2006, 71, 8298-8301 https://doi.org/10.1021/jo061234p
  6. Zhan, Z.-p.; Yang, W.-z.; Yang, R.-f.; Yu, J.-l.; Li, J.-p.; Liu, H.-j. Chem. Commun. 2006, 3352- 3354
  7. Sanz, R.; Martinez, A.; Alvarez-Gutierrez, J. M.; Rodriguez, F. Eur. J. Org. Chem. 2006, 1383-1386.
  8. Karunakar, G. V.; Periasamy, M. J. Org. Chem. 2006, 71, 7463-7466 https://doi.org/10.1021/jo060683m
  9. Srihari, P.; Bhunia, D. C.; Sreedhar, P.; Mandal, S. S.; Reddy, J. S. S.; Yadav, J. S. Tetrahedron Lett. 2007, 48, 8120-8124. Propargylic acetates was also used: https://doi.org/10.1016/j.tetlet.2007.09.123
  10. Zhan, Z.-P.; Cui, Y.-Y.; Liu, H.-J. Tetrahedron Lett. 2006, 47, 9143-9146 https://doi.org/10.1016/j.tetlet.2006.10.038
  11. Zhan, Z.-P.; Liu, H.-J. Synlett 2006, 2278-2280. Very recently a new method involving the use of InBr3 has been added:
  12. Yadav, J. S.; Subba Reddy, B. V.; Raghavendra Rao, K. V.; Narayana Kumar, G. G. K. S. Synthesis 2007, 3205-3210
  13. Li, C.; Wang, J. J. Org. Chem. 2007, 72, 7431-7434 https://doi.org/10.1021/jo0709192
  14. Olah, G. A.; Krishnamurti, R.; Prakash, G. K. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, Chapter 1.8
  15. Olah, G. A. Friedel- Crafts and Related Reactions; Interscience Publishers: New York, 1964
  16. Stamm, H.; Onistschenko, A.; Buchholz, B.; Mall, T. J. Org. Chem. 1989, 54, 193-199 https://doi.org/10.1021/jo00262a042
  17. Kim, J. N.; Chung, K. H.; Ryu, E. K. Tetrahedron Lett. 1994, 35, 903-904 https://doi.org/10.1016/S0040-4039(00)75994-6
  18. Chung, G. H.; Kim, J. N.; Ryu, E. K. Tetrahedron Lett. 1994, 35, 2913-2914 https://doi.org/10.1016/S0040-4039(00)76658-5
  19. Lee, H. J.; Seong, M. R.; Kim, J. N. Tetrahedron Lett. 1998, 39, 6223- 6226 https://doi.org/10.1016/S0040-4039(98)01280-5
  20. Lee, H. J.; Seong, M. R.; Song, H. N.; Kim, J. N. Bull. Korean Chem. Soc. 1999, 20, 267-268
  21. For the synthesis of N-tosylpropargyl amines and related compounds, see: Lee, K. Y.; Lee, C. G.; Na, J. E.; Kim, J. N. Tetrahedron Lett. 2005, 46, 69-74 and further references cited therein https://doi.org/10.1016/j.tetlet.2004.11.046
  22. Shi, Z.; He, C. J. Org. Chem. 2004, 69, 3669-3671 https://doi.org/10.1021/jo0497353
  23. Asao, N.; Takahashi, K.; Lee, S.; Kasahara, T.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 12650-12651 https://doi.org/10.1021/ja028128z
  24. Hashimi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem. Int. Ed. 2000, 39, 2285- 2288 https://doi.org/10.1002/1521-3773(20000703)39:13<2285::AID-ANIE2285>3.0.CO;2-F
  25. Guo, S.; Song, F.; Liu, Y. Synlett 2007, 964-968
  26. Li, Z.; Capretto, D. A.; Rahaman, R. O.; He, C. J. Am. Chem. Soc. 2007, 129, 12058-12059 https://doi.org/10.1021/ja0724137
  27. Jin, T.; Yamamoto, Y. Org. Lett. 2007, 9, 5259-5262 https://doi.org/10.1021/ol702455v
  28. Tang, J.-M.; Bhunia, S.; Sohel, S. M. A.; Lin, M.-Y.; Liao, H.-Y.; Datta, S.; Das, A.; Liu, R.-S. J. Am. Chem. Soc. 2007, 129, 15677-15683, and further references cited therein https://doi.org/10.1021/ja076175r

Cited by

  1. ) Bond Cleavage in Generation of Iminium Intermediates vol.132, pp.15, 2010, https://doi.org/10.1021/ja9109055
  2. Catalytic decarboxylative alkylation of β-keto acids with sulfonamides via the cleavage of carbon–nitrogen and carbon–carbon bonds vol.47, pp.29, 2011, https://doi.org/10.1039/c1cc12790j
  3. -Benzylic Sulfonamides through Carbon–Nitrogen Bond Cleavage vol.76, pp.19, 2011, https://doi.org/10.1021/jo2014142
  4. Electrophilic chemistry of propargylic alcohols in imidazolium ionic liquids: Propargylation of arenes and synthesis of propargylic ethers catalyzed by metallic triflates [Bi(OTf)3, Sc(OTf)3, Yb(OTf)3], TfOH, or B(C6F5)3 vol.9, pp.7, 2011, https://doi.org/10.1039/c0ob00872a
  5. C–N bonds for access to highly enantioenriched N-benzylic sulfonamides vol.48, pp.6, 2012, https://doi.org/10.1039/C1CC16630A
  6. Ferric chloride-catalyzed C–N bond cleavage for the cyclization of arylallenes leading to polysubstituted indenes vol.48, pp.88, 2012, https://doi.org/10.1039/c2cc36048a
  7. -Benzylic Sulfonamides with Alkenes vol.2, pp.4, 2013, https://doi.org/10.1002/ajoc.201300020
  8. Iron-Catalyzed CC Bond Cleavage and CN Bond Formation vol.355, pp.1, 2013, https://doi.org/10.1002/adsc.201200324
  9. Transition-Metal-Catalyzed Cleavage of C–N Single Bonds vol.115, pp.21, 2015, https://doi.org/10.1021/acs.chemrev.5b00386
  10. metal–allenylidene intermediates: a theoretical perspective vol.8, pp.1, 2018, https://doi.org/10.1039/C7CY01382E
  11. Catalytic Propargylic Substitution Reactions vol.1, pp.3, 2009, https://doi.org/10.1002/cctc.200900214
  12. -Catalyzed Propargylation of Arenes with N-Tosylpropargyl Amine: Synthesis of 1,3-Diarylpropynes. vol.40, pp.1, 2009, https://doi.org/10.1002/chin.200901093
  13. Catalytic CN Bond Alkynylation of N‐Benzylic Sulfonamides with Terminal Alkynes vol.32, pp.5, 2008, https://doi.org/10.1002/cjoc.201400194