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http://dx.doi.org/10.5012/bkcs.2007.28.9.1515

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)
Publication Information
Bulletin of the Korean Chemical Society / v.28, no.9, 2007 , pp. 1515-1518 More about this Journal
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
Copper(I) halide-dimethyl sulfide complex; DMSO; Benzyl halide;
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1 Kokoreva, S. G.; Nifontova, G. A.; Korableva, L. G.; Sikorenko, Y. B.; Lavrentev, I. P. Zh. Neorg. Khim. 1995, 40, 1320-1324
2 Park, K. H.; Cho, Y. H.; Jang, E. J. Bull. Korean Chem. Soc. 1996, 17(2), 179-182   DOI   ScienceOn
3 Roe, A. Org. React. 1952, 5, 193.
4 Baldwin, J. E.; Spivey, A. C.; Schofield, C. J.; Sweeney, J. B. Tetrahedron 1993, 49, 6309-6330   DOI   ScienceOn
5 Kharitonov, D. N. Russ. J. Coord. Chem. 1996, 22, 668-670
6 House, H. O.; Chu, C.-Y.; Wilkins, J. M.; Umen, M. J. J. Org. Chem. 1975, 40, 1460-1469   DOI
7 Wuts, P. G. M. Synth. Commun. 1981, 11(2), 139-140   DOI   ScienceOn
8 Theis, A. B.; Townsend, C. A. Synth. Commun. 1981, 11(2), 157-166   DOI   ScienceOn
9 Park, K. H.; So, M. S.; Kim, Y. W. Bull. Korean Chem. Soc. 2005, 26, 1491-1492   DOI   ScienceOn
10 Helm, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1957, 114, 6227-6238   DOI
11 Ganem, B.; Boeckman Jr., R. K. Tetrahedron Lett. 1974, 11, 917-920
12 Ebert, G. W.; Rieke, R. D. J. Org. Chem. 1984, 49, 5280-5282   DOI
13 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   DOI   ScienceOn
14 Kornblum, N.; Jones, W. J.; Anderson, G. J. J. Am. Chem. Soc. 1959, 81, 4113-4114   DOI
15 Danes, A. M.; Abell, A. D. Org. Biomol. Chem. 2004, 2, 2371-2375   DOI   ScienceOn
16 Nace, H. R.; Monagle, J. J. J. Org. Chem. 1959, 24, 1792-1793   DOI