DOI QR코드

DOI QR Code

Sonochemical Reformatsky Reaction Using Indium


초록

Sonochemical Reformatsky reaction of aldehydes or ketones with ethyl bromoacetate in the presence of indium afforded $\beta-hydroxyesters$ in good to excellent yields under mild conditions. 2- or 3-Hydroxybenzaldehyde that contains an acidic hydrogen r eacted with ethyl bromoacetate to provide the desired compounds with the same efficiency. In the case of ethyl 2-bromopropanoate and ethyl 2-bromo-2-methylpropanoate, the desired products were obtained in good yields. Reaction of aldehyde with indium reagent in the presence of ketone group proceeded chemoselectively.

키워드

참고문헌

  1. Shriner, R. L. Org. React. 1946, 1, 1.
  2. Rathke, M. W. Org. React. 1975, 22, 423.
  3. Gensler, W. J. Chem. Rev. 1957, 57, 265.
  4. Diaper, D. G. M.; Kuksis, A. Chem. Rev. 1959, 59, 89. https://doi.org/10.1021/cr50025a003
  5. Becker, D.; Brodsky, N.; Kalo, I. J. Org. Chem. 1978, 43, 2557. https://doi.org/10.1021/jo00407a002
  6. Barco, A.; Benett, S.; Pollini, G. P. J. Org. Chem. 1980, 45, 4776. https://doi.org/10.1021/jo01311a047
  7. Klipa, D. K.; Hart, H. J. Org. Chem. 1981, 46, 2815. https://doi.org/10.1021/jo00326a050
  8. West, F. G.; Gunawardena, G. V. J. Org. Chem. 1993, 58, 5043. https://doi.org/10.1021/jo00071a008
  9. Witzemann, J. S.; Nottingham, W. D. J. Org. Chem. 1989, 54, 3258 https://doi.org/10.1021/jo00275a006
  10. March, J. Advanced Organic Chemistry; Wiley: New York, 1992; p 929.
  11. Marioka, K.; Hashimoto, S.; Kitagawa, Y.; Yamamoto, H.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 7705. https://doi.org/10.1021/ja00465a049
  12. Harada, T.; Mukaiyama, T. Chem. Lett. 1982, 161.
  13. Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. https://doi.org/10.1021/jo00195a006
  14. Nokami, J.; Tamaoka, T.; Ogawa, H.; Wakabayashi, S. Chem. Lett. 1986, 541.
  15. Shen, Z.; Zhang, J.; Zou, H.; Yang, M. Tetrahedron Lett. 1997, 38, 2733. https://doi.org/10.1016/S0040-4039(97)00456-5
  16. Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 38, 1363. https://doi.org/10.1016/S0040-4039(96)02494-X
  17. Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 38, 4387. https://doi.org/10.1016/S0040-4039(97)00952-0
  18. Chao, L.-C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253. https://doi.org/10.1021/jo00903a031
  19. Araki, S.; Ito, H.; Butsugan, Y. Synth. Commun. 1988, 18, 453. https://doi.org/10.1080/00397918808064009
  20. Araki, S.; Ito, H.; Katsumura, N.; Butsugan, Y. J. Organomet. Chem. 1989, 369, 291. https://doi.org/10.1016/0022-328X(89)85180-0
  21. Araki, S.; Katsumura, N.; Kawasaki, K.; Butsugan, Y. J. Chem. Soc. Perkin Trans. 1 1991, 499.
  22. Johar, P. S.; Araki, S.; Butsugan, Y. J. Chem. Soc. Perkin Trans. 1 1992, 711.
  23. Schick, H.; Ludwig, R.; Schwarz, K.-H.; Kleiner, K.; Kunath, A. Angew. Chem. Int. Ed. Engl. 1993, 32, 1191. https://doi.org/10.1002/anie.199311911
  24. Cahiez, G.; Chavant, P.-Y. Tetrahedron Lett. 1989, 30, 7373. https://doi.org/10.1016/S0040-4039(00)70700-3
  25. Kagan, H. B.; Namy, J.-L.; Girard, P. Tetrahedron 1981, 37, 175. https://doi.org/10.1016/0040-4020(81)85053-3
  26. Tabuchi, T.; Kawamura, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 3889. https://doi.org/10.1016/S0040-4039(00)83907-6
  27. Molander, G. A.; Etter, J. B. J. Am. Chem. Soc. 1987, 109, 6556. https://doi.org/10.1021/ja00255a076
  28. Huang, X.; Xie, L.; Wu, H. Tetrahedron Lett. 1987, 28, 801. https://doi.org/10.1016/S0040-4039(01)80993-X
  29. Fustner, A. Synthesis 1989, 571.
  30. Fustner, A. Angew. Chem. Int. Ed. Engl. 1993, 32, 164. https://doi.org/10.1002/anie.199301641
  31. Rieke, R. D.; Uhm, S. J. Synthesis 1975, 452.
  32. Mason, T. J.; Lorimer, J. P. Sonochemistry: Theory, Applications and Uses of Ultrasound in Chemistry; Ellis Horwood Limited: Chichester, 1988.
  33. Han, B. H.; Boudjouk, P. J. Org. Chem. 1982, 47, 5030. https://doi.org/10.1021/jo00146a044
  34. Nishiyama, T.; Woodhall, J. F.; Lawson, E. N.; Kitching, W. J. Org. Chem. 1989, 54, 2184.
  35. Lee, P. H.; Bang, K.; Lee, K.; Lee, C.-H.; Chang, S. Tetrahedron Lett. 2000, 41, 7521. https://doi.org/10.1016/S0040-4039(00)01290-9
  36. Lee, P. H.; Bang, K.; Ahn, H.; Lee, K. Bull. Korean Chem. Soc. 2001, 22, 1385.
  37. Lee, P. H.; Seomoon, S.; Lee, K. Bull. Korean Chem. Soc. 2001, 22, 1380.
  38. Lee, P. H.; Lee, K.; Sung, S.-Y.; Chang, S. J. Org. Chem. 2001, 66, 8646. https://doi.org/10.1021/jo0105641
  39. Lee, P. H.; Lee, K.; Kim, S. Org. Lett. 2001, 3, 3205. https://doi.org/10.1021/ol016542i
  40. Lee, P. H.; Sung, S.-Y.; Lee, K. Org. Lett. 2001, 3, 3201. https://doi.org/10.1021/ol016532h
  41. Lee, P. H.; Lee, K.; Chang, S. Synth. Commun. 2001, 31, 3189. https://doi.org/10.1081/SCC-100105896
  42. Lee, P. H.; Ahn, H.; Lee, K.; Sung, S.-Y.; Kim, S. Tetrahedron Lett. 2001, 42, 37. https://doi.org/10.1016/S0040-4039(00)01872-4
  43. Lee, P. H.; Sung, S.-Y.; Lee, K.; Chang, S. Synlett 2002, 146.
  44. Lee, P. H.; Bang, K.; Lee, K.; Sung, S.-Y.; Chang, S. Synth. Commun. 2001, 31, 3781. https://doi.org/10.1081/SCC-100108228

피인용 문헌

  1. Tetraorganoindates as Nucleophilic Coupling Partners in Pd-Catalyzed Cross-Coupling Reactions vol.5, pp.26, 2003, https://doi.org/10.1021/ol035883o
  2. Cyclization of 1-Bromo-2,7- and 1-Bromo-2,8-Enynes Mediated by Indium vol.6, pp.26, 2004, https://doi.org/10.1021/ol048175r
  3. Cp2ZrCl2-induced Reformatsky and Barbier reactions on isatins: an efficient synthesis of 3-substituted-3-hydroxyindolin-2-ones vol.25, pp.6, 2011, https://doi.org/10.1002/aoc.1789
  4. Sonolysis of Short-Chain Organic Dicarboxylic Acid Solutions vol.50, pp.7, 2011, https://doi.org/10.1143/JJAP.50.07HE15
  5. : Application of Crotylsilanes Accessed by Enantioselective Rh(II) or Cu(I) Promoted Carbenoid Si–H Insertion vol.76, pp.24, 2011, https://doi.org/10.1021/jo202119p
  6. -Amino Esters via a Sonocatalyzed Reformatsky Reaction vol.14, pp.1, 2012, https://doi.org/10.1021/ol202969w
  7. Organoindium Reagents: The Preparation and Application in Organic Synthesis vol.113, pp.1, 2013, https://doi.org/10.1021/cr300051y
  8. Comparative Studies on Conventional and Ultrasound-Assisted Synthesis of Novel Homoallylic Alcohol Derivatives Linked to Sulfonyl Dibenzene Moiety in Aqueous Media vol.2013, pp.2090-9071, 2013, https://doi.org/10.1155/2013/364036
  9. Sonolysis of Short-Chain Organic Dicarboxylic Acid Solutions vol.50, pp.7S, 2013, https://doi.org/10.7567/JJAP.50.07HE15
  10. Regioselective allylgallation of terminal alkynes pp.14, 2005, https://doi.org/10.1039/b417975g
  11. Enantioselective Reformatsky Reaction Using Cinchona Alkaloids as Chiral Ligands vol.47, pp.6, 2002, https://doi.org/10.5012/jkcs.2003.47.6.597
  12. Sonochemical Reformatsky Reaction Using Indium. vol.34, pp.8, 2002, https://doi.org/10.1002/chin.200308058
  13. Indium-Mediated &bgr;-Allylation, &bgr;-Propargylation, and &bgr;-Allenylation onto &agr;,&bgr;-Unsaturated Ketones: Reactions of in-Situ-Generated 3-tert-Butyldimethylsilyloxyalk-2-enylsulfonium Sal vol.125, pp.32, 2003, https://doi.org/10.1021/ja035988m
  14. Palladium-Catalyzed Homocoupling Reaction of 1-Iodoalkynes: A Simple and Efficient Synthesis of Symmetrical 1,3-Diynes vol.68, pp.18, 2002, https://doi.org/10.1021/jo034727s
  15. Synthesis of Chromane Derivatives via Indium-mediated Intramolecular Allenylation and Allylation to Imines vol.25, pp.11, 2002, https://doi.org/10.5012/bkcs.2004.25.11.1627
  16. Regioselective Addition Reactions of the Organoindium Reagents onto α,β-Unsaturated Ketones vol.25, pp.11, 2002, https://doi.org/10.5012/bkcs.2004.25.11.1687
  17. Preparation of Chromane Derivatives via Indium-mediated Intramolecular Allylation Reactions vol.25, pp.8, 2002, https://doi.org/10.5012/bkcs.2004.25.8.1123
  18. The Reformatsky reaction in organic synthesis. Recent advances vol.60, pp.42, 2002, https://doi.org/10.1016/j.tet.2004.07.018
  19. Facile Synthesis of β-Ketoesters by Indium-Mediated Reaction of Acyl Cyanides with Ethyl Bromoacetate under Ultrasonication vol.26, pp.6, 2005, https://doi.org/10.5012/bkcs.2005.26.6.878
  20. Indium and Gallium-Mediated Addition Reactions vol.28, pp.1, 2007, https://doi.org/10.5012/bkcs.2007.28.1.017
  21. Cooperative Catalysis by Indium and Palladium for the Allyl Cross-Coupling Reactions vol.28, pp.11, 2002, https://doi.org/10.5012/bkcs.2007.28.11.1929
  22. Palladium-Catalyzed Cross-Coupling Reaction and Gold-Catalyzed Cyclization for Preparation of Ethyl 2-Aryl 2,3-Alkadienoates and α-Aryl γ-Butenolides vol.32, pp.8, 2002, https://doi.org/10.5012/bkcs.2011.32.8.2911