Copper-catalyzed synthesis of diaryl selenide from aryl iodide and diphenyl diselenide using magnesium metal

Synlett

Volumn , Issue 6, 2003, Pages 829-832

  Taniguchi, Nobukazu ^a   Onami, Tetsuo ^a  

^a FUKUSHIMA MEDICAL UNIVERSITY   (Japan)

Author keywords

Aryl iodide; Copper catalyst; Diaryl selenide; Diphenyl diselenide; Magnesium

Indexed keywords

BIPHENYL; COPPER; IODIDE; MAGNESIUM; SELENIDE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; GEL CHROMATOGRAPHY; REACTION ANALYSIS;

EID: 0037617939     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (26)

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10. Some examples of phenylselenation of alkyl halide with stoichiometric metal reagent and diphenyl diselenide are known: (a) Okamoto, Y.; Yano, T. J. Organomet. Chem. 1971, 29, 99. (b) Bao, W.; Zheng, Y.; Zhang, Y.; Zhou, J. Thetrahedron Lett. 1996, 37, 9333. (c) Bao, W.; Zhang, Y. Synlett 1996, 1187. (d) Nishino, Y. T.; Okada, M.; Kuroki, T.; Watanabe, T.; Nishiyama, Y.; Sonoda, N. J. Org. Chem. 2002, 67, 8696.
11. Some examples of phenylselenation of alkyl halide with stoichiometric metal reagent and diphenyl diselenide are known: (a) Okamoto, Y.; Yano, T. J. Organomet. Chem. 1971, 29, 99. (b) Bao, W.; Zheng, Y.; Zhang, Y.; Zhou, J. Thetrahedron Lett. 1996, 37, 9333. (c) Bao, W.; Zhang, Y. Synlett 1996, 1187. (d) Nishino, Y. T.; Okada, M.; Kuroki, T.; Watanabe, T.; Nishiyama, Y.; Sonoda, N. J. Org. Chem. 2002, 67, 8696.
12. Some examples of phenylselenation of alkyl halide with stoichiometric metal reagent and diphenyl diselenide are known: (a) Okamoto, Y.; Yano, T. J. Organomet. Chem. 1971, 29, 99. (b) Bao, W.; Zheng, Y.; Zhang, Y.; Zhou, J. Thetrahedron Lett. 1996, 37, 9333. (c) Bao, W.; Zhang, Y. Synlett 1996, 1187. (d) Nishino, Y. T.; Okada, M.; Kuroki, T.; Watanabe, T.; Nishiyama, Y.; Sonoda, N. J. Org. Chem. 2002, 67, 8696.
13. As an example using efficiently diphenyl diselenide, the palladium-catalyzed addition to acetylene compounds has been reported: (a) Kuniyasu, H.; Ogawa, A.; Miyazaki, S.-i.; Ryu, I.; Kanbe, N.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 9796. (b) Ogawa, A.; Kuniyasu, H.; Sato, K.; Sonoda, N.; Hirao, T. J. Org. Chem. 1997, 62, 8361.
14. As an example using efficiently diphenyl diselenide, the palladium-catalyzed addition to acetylene compounds has been reported: (a) Kuniyasu, H.; Ogawa, A.; Miyazaki, S.-i.; Ryu, I.; Kanbe, N.; Sonoda, N. J. Am. Chem. Soc. 1991, 113, 9796. (b) Ogawa, A.; Kuniyasu, H.; Sato, K.; Sonoda, N.; Hirao, T. J. Org. Chem. 1997, 62, 8361.
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18. In the experiment of entry 1 in Tables 1, 97% 2-iodotoluene and 89% diphenyl diselenide were recovered; no other products were obtained at all.
19. The magnesium metal could not reduce diphenyl diselenide under our conditions. In entry 2 in Tables 1, 97% 2-iodotoluene and 96% diphenyl diselenide were recovered.
20. The preparation of ArMgI from ArI and Mg could not be carried out in DMF: (a) Olah, G. A.; Ohannesian, L.; Arvanaghi, M. Chem. Rev. 1987, 87, 671. (b) Organomagnesium Methods in Organic Synthesis; Wakefield, B. J., Ed.; Academic Press: San Diego, 1995.
21. The preparation of ArMgI from ArI and Mg could not be carried out in DMF: (a) Olah, G. A.; Ohannesian, L.; Arvanaghi, M. Chem. Rev. 1987, 87, 671. (b) Organomagnesium Methods in Organic Synthesis; Wakefield, B. J., Ed.; Academic Press: San Diego, 1995.
22. 2 produced a green precipitate. The structure of this compound is now under investigation.
23. 2O and PhSeH in EtOH for 24 h.
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26. 3Se: C, 51.84; H, 3.01. Found: C, 51.69; H, 3.14.