One-pot synthetic method of unsymmetrical diorganyl selenides: Reaction of diphenyl diselenide with alkyl halides in the presence of lanthanum metal

Journal of Organic Chemistry

Volumn 67, Issue 24, 2002, Pages 8696-8698

  Nishino, Toshiki ^a   Okada, Mitsuo ^a   Kuroki, Takamasa ^a   Watanabe, Toshihisa ^a   Nishiyama, Yutaka ^a   Sonoda, Noboru ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

REACTION PATHWAYS;

ADDITION REACTIONS; LANTHANUM; SELENIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

HALIDE; LANTHANUM; METAL; SELENIDE;

ANALYTIC METHOD; ARTICLE; ASYMMETRIC SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; COMPLEX FORMATION; DIMERIZATION; DRUG ISOLATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0037195710     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026032h     Document Type: Article

References (23)

1. (a) Krief, A.; Hevesi, L. In Organoselenium Chemistry; Springer-Verlag: Berlin, 1988; Vol. 1.
2. (b) Paulmier, C. In Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press: Oxford, 1986.
3. (c) Patai, S.; Rappoport, Z. In The Chemistry of Organic Selenium and Tellurium Compounds; Wiley & Sons: New York, 1986 and 1987; Vols. 1 and 2.
4. (d) Krief, A. In Comprehensive Organometallic Chemistry; Trost, B. M., Eds.; Pergamon Press: Oxford, 1991; pp 85-192 and references therein.
5. 2. However, these methods required the handling of reagents unstable toward air and/or moisture and the poisonous reagents. Furthermore, to the best of our knowledge, there are no examples of methods for generating lanthanoid selenolate anion by use of other lanthanoid metals.
6. Wang, L.; Zhang, Y. Heteroat. Chem. 1999, 10, 203.
7. (a) Fukuzawa, S.; Niimoto, Y.; Fujinami, T.; Sakai, S. Heteroat. Chem. 1990, 1, 491.
8. (b) Sekiguchi, M.; Tanaka, H.; Takemi, N.; Ogawa, A.; Ryu, I.; Sonoda, N. Heteroat. Chem. 1991, 2, 427.
9. (c) Zhang, Y.; Yu, Y.; Lin, R. Synth. Commun. 1993, 23, 189.
10. We have already shown that the addition of a catalytic amount of iodine dramatically enhanced the reductive dimerization of carbonyl compounds, imines, and alkyl halides.
11. Nishino, T.; Nishiyama, Y.; Sonoda, N. Heteroat. Chem. 2000, 11, 81.
12. Nishino, T.; Nishiyama, Y.; Sonoda, N. Heteroat. Chem. 2002, 13, 131.
13. Nishino, T.; Watanabe, T.; Okada, M.; Nishiyama, Y.; Sonoda, N. J. Org. Chem. 2002, 67, 966.
14. Mashima, K.; Nakayama, Y.; Fukumoto, H.; Kanehisa, N.; Kai, Y.; Nakamura, A. J. Chem. Soc., Chem. Commun. 1994, 2523.
15. Fujiwara et al. reported that the reaction of diaryl and dialkyl disulfide with ytterbium metal was activated by benzophenone to afford ytterbium(III) thiolates. The thiolates thus formed in situ were reacted with enones to give Michael adducts. See: Taniguchi, Y.; Maruo, M.; Takaki, K.; Fujiwara, Y. Tetrahedron Lett. 1994, 35, 7789.
16. It was known that the reduction of organic compounds with samarium(II) iodide was promoted by the addition of HMPA. However, the reductive coupling of carbonyl compounds with lanthanum metal was not accelerated by the addition of HMPA.
17. It is well-known that the nucleophilic addition of organometallic compounds such as alkyllithium compounds is promoted by the addition of HMPA and TMEDA due to the deaggregation of organometallic compound by these reagents. From the background, we suggested that the deaggregation of lanthanum selenolate with HMPA or TMEDA raised the nucleophilicity of selenolate.
18. (a) Otsubo, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 5763.
19. (b) Otsubo, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1987, 28, 4437.
20. (c) Inanaga, J.; Ishikawa, M.; Yamaguchi, M. Chem. Lett. 1987, 1485.
21. (d) Hou, Z.; Wakatuki, Y. J. Chem. Soc., Chem. Commun. 1994, 1205.
22. (e) Hou, Z.; Zhang, Y.; Wakatuki, Y. Bull. Chem. Soc. Jpn. 1997, 70, 149.
23. Reich, H. J.; Renga, J. M.; Reich, I. L. J. Am. Chem. Soc. 1975, 97, 5434.