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Facile Preparation of Copper(I) Halide-Dimethyl Sulfide Complex and Its Application

  • Park, Il-Hyun (Division of Chemistry & Biochemistry, Chungnam National University) ;
  • So, Myung-Sub (Gunsan Jeil High School) ;
  • Park, Koon-Ha (Division of Chemistry & Biochemistry, Chungnam National University)
  • Published : 2007.09.20

Abstract

A preparative method of Me2SCuX (X = Cl, Br) via one-pot reaction was developed from common chemicals such as benzyl halide, DMSO, and Cu(0). In the reaction mixture small molecules such as methyl halide and dimethyl sulfide etc. were efficiently generated in situ, resulting in the formation of Me2SCuX. Oxidation of Cu(0) in reacting with both benzyl halide (starting material) and methyl halide (in situ generated product) to Cu(I) followed by complexing with dimethyl sulfide (in situ generated product) could explain the formation of Me2SCuX. In particular we found out that heterogeneous reaction of Me2SCuX and arenediazonium tetrafluoroborate in acetonitrile was so effective to afford corresponding bromoaromatics under mild conditions.

Keywords

References

  1. Danes, A. M.; Abell, A. D. Org. Biomol. Chem. 2004, 2, 2371-2375 https://doi.org/10.1039/b407659a
  2. Baldwin, J. E.; Spivey, A. C.; Schofield, C. J.; Sweeney, J. B. Tetrahedron 1993, 49, 6309-6330 https://doi.org/10.1016/S0040-4020(01)87968-0
  3. Kharitonov, D. N. Russ. J. Coord. Chem. 1996, 22, 668-670
  4. House, H. O.; Chu, C.-Y.; Wilkins, J. M.; Umen, M. J. J. Org. Chem. 1975, 40, 1460-1469 https://doi.org/10.1021/jo00898a019
  5. Wuts, P. G. M. Synth. Commun. 1981, 11(2), 139-140 https://doi.org/10.1080/00397918108064294
  6. Theis, A. B.; Townsend, C. A. Synth. Commun. 1981, 11(2), 157-166 https://doi.org/10.1080/00397918108064297
  7. Park, K. H.; So, M. S.; Kim, Y. W. Bull. Korean Chem. Soc. 2005, 26, 1491-1492 https://doi.org/10.5012/bkcs.2005.26.10.1491
  8. Kokoreva, S. G.; Nifontova, G. A.; Korableva, L. G.; Sikorenko, Y. B.; Lavrentev, I. P. Zh. Neorg. Khim. 1995, 40, 1320-1324
  9. Park, K. H.; Cho, Y. H.; Jang, E. J. Bull. Korean Chem. Soc. 1996, 17(2), 179-182 https://doi.org/10.1007/BF02707140
  10. Roe, A. Org. React. 1952, 5, 193.
  11. Kornblum, N.; Jones, W. J.; Anderson, G. J. J. Am. Chem. Soc. 1959, 81, 4113-4114 https://doi.org/10.1021/ja01524a080
  12. Nace, H. R.; Monagle, J. J. J. Org. Chem. 1959, 24, 1792-1793 https://doi.org/10.1021/jo01093a608
  13. Helm, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1957, 114, 6227-6238 https://doi.org/10.1021/ja00041a047
  14. Ganem, B.; Boeckman Jr., R. K. Tetrahedron Lett. 1974, 11, 917-920
  15. Ebert, G. W.; Rieke, R. D. J. Org. Chem. 1984, 49, 5280-5282 https://doi.org/10.1021/jo00200a064
  16. Chu, C.-K.; Kim, J.-H.; Kim, D. W.; Chung, K.-Y.; Katzenellenbogen, J. A.; Chi, D. Y. Bull. Korean Chem. Soc. 2005, 26, 599-602 https://doi.org/10.5012/bkcs.2005.26.4.599

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