A Bimetallic Palladium(II) Catalyzed Synthesis of 1,2-Dibromo Compounds

• Autorzy: Qaseer H.
• Języki publikacji: EN

Abstrakty

EN

A bimetallic palladium(II) catalyst containing a triketone ligand and a bridging dinitrogen ligand oxidizes aromatic and cyclic aliphatic olefins in bromide-containing aqueous-THF to 1,2-dibromo compounds and bromohydrins. With aromatic olefins, the 1,2-dibromo products were obtained in a 70–80% yield and the bromohydrins in a 10–15% yield; this observation is opposition to that obtained in chloride containing medium where the chlorohydrin product predominates. The oxidation of 2,3-dihydrofuran gave trans-2,3-dibromotetrahydrofuran, 3-oxotetrahydrofuran, and 3-bromo-2- hydroxytetrahydrofuran in relative yields of 75%, 15%, and 10%, respectively. On the other hand, the oxidation of cyclopentene and cyclohexene affords only trans-1,2- dibromo products in about 90% yield. The stereochemistry is consistent with an anti-attack of bromide followed by decomposition involving attack of bromide from the coordination sphere of the Pd(II). The procedure outlin

Słowa kluczowe

EN

palladium(II); atalysis; 1,2-dibromides, bromohydrin

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2007
• Tom: Vol. 81, nr 1
• Strony: 31--38
• Opis fizyczny: Bibliogr. 13 poz., rys.

Twórcy

autor

Qaseer H.

• Department of Chemistry, Mu’tah University, P.O. Box 37, Mu’tah, Al-Karak, Jordan

Bibliografia

• 1. a) El-Qisairi A., Hamed O. and Henry P.M., J. Org. Chem., 63, 2790 (1998); b) Hamed O. and Henry RM., Organometallics, 17, 5184 (1998); c)  El-Qisairi A.K. and Henry RM., J. Organomet. Chem., 603, 50 (2000); d) El-Qisairi A.K., Qaseer H.A. and Henry RM., J. Organomet. Chem., 656, 168 (2002).
• 2. El-Qisairi A.K., Qaseer H.A., Katsigras G., Lorenzi R, Trivedi U., Tracz S., Hartman A., Miller J.A. and Henry RM., Org. Lett., 5, 439 (2003).
• 3. a) Hamed O., El-Qisairi A. and Henry RM., J. Org. Chem., 66, 180 (2001); "b) Hamed O., El-Qisairi A. and Henry RM., Tetrahedron Lett., 41, 3021 (2000).
• 4. El-Qisairi A.K. and Qaseer H.A., J. Organomet. Chem., 659, 50 (2002).
• 5. Dewkar G.K., Narina S.V. and Sudali A., Org. Lett., 5, 4501 (2003).
• 6. Henry RM., Palladium Catalyzed Oxidation of Hydrocarbon, D. Reidel, Dordrecht, Holland, 1980, pp. 73-74.
• 7. Bovey F., Nuclear Magnetic Resonance Spectroscopy, Academic Press, San Diego, 1988, p. 617.
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• 9. a) Francis J.W. and Henry RM., J. Mol. Catal. A. Chem., 99, 77 (1995); b) Francis J.W. and Henry RM., J. Mol. Catal. A. Chem., 101, 317 (1996).
• 10. For a similar apparatus see: Henry RM., Palladium Catalyzed Oxidation of Hydrocarbon, D. Reidel, Dordrecht, Holland, 1980, p. 57.
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• 13. Katritzky A.R. and Lloyd J.M., J. Chem. Soc. Perkin Trans., l, 2347 (1982).