New Version of the TEMPO-based Catalytic System for the Oxidation of Alcohols to Aldehydes

• Autorzy: Kowalczyk R. , Skarżewski J.
• Języki publikacji: EN

Abstrakty

EN

A new chemoselective catalytic system for the title oxidation was developed using methyltrioxorhenium (3 mol%), KBr (10 mol%) and TEMPO (3 mol%) as co-catalysts and Oxone_ as a terminal oxidant.

Słowa kluczowe

EN

catalytic oxidation; TEMPO; methyltrioxorhenium; aldehydes

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2002
• Tom: Vol. 76 / nr 10
• Strony: 1413--1417
• Opis fizyczny: Bibliogr. 11 poz., rys.

Twórcy

autor

Kowalczyk R.

• Institute of Organic Chemistry, Biochemistry and Biotechnology, Wrocław University of Technology, 50-370 Wrocław, Poland

autor

Skarżewski J.

• Institute of Organic Chemistry, Biochemistry and Biotechnology, Wrocław University of Technology, 50-370 Wrocław, Poland

Bibliografia

• 1. Sheldon R.A. and Kochi J.K., Metal-Catalysed Oxidations in Organic Chemistry, Academic Press, NY, 1981; Hudlicky M., Oxidations in Organic Chemistry, ACS, Washington, DC, 1990; Ley S.V., Norman J., Griffith W.P. and Marsden S.P., Synthesis, 639 (1994); Sato K., Aoki M., Takagi J., Zimmermann K. and Noyori R., Bull. Chem. Soc. Jap., 72, 2287 (1999) and references cited therein.
• 2. Siedlecka R, Skarżewski J. and Młochowski J., Tetrahedron Lett., 31, 2177 (1990).
• 3. Anelli P.L., Biffi C., Montanari F. and Quici S., J. Org. Chem., 52,2559 (1987).
• 4. For reviews on the use of oxoammonium salts in oxidation, see: Bobbitt J.M. and Flores M.C.L., Heterocycles, 27,509 (1988); Yamaguchi M., Miyazawa T., Takata T. and Endo T., Pure Appl. Chem., 62,217 (1990); De Nooy A.E.J., Besemer A.C. and van Bekkum H., Synthesis, 1153 (1996); Adam W., Saha-Moller S.R. and Ganeshpure P.A., Chem. Rev., 101, 3499 (2001).
• 5. Herrmann W.A., Zoller J.P. and Fischer R.W., J.Organometal. Chem., 579,404 (1999); for a review on the catalytic use of MTO, see: Owens G.S., Arias J. and Abu-Omar M.M., Catal. Today, 55,317 (2000).
• 6. Bolm C., Magnus A.S. and Hildebrand J., Org. Lett., 2, 1173 (2000).
• 7. De Nooy A.E.J., Besemer A.C. and van Bekkum H., Tetrahedron, 51, 8023 (1995).
• 8. Fortnum D.H., Battaglia C.J., Cohen S.R. and Edwards J.O., J Am. Chem. Soc., 82, 778 (1960).
• 9. Even in the presence ofMTO, faster addition ofcaroate resulted in some destruction of TEMPO and gave less yield of undecanal, cf. Table 1, entries 3 and 4.
• 10. Siedlecka R., Doctoral Thesis, Institute of Organic and Physical Chemistry, Wroclaw University of Technology, Wroclaw, 1992.
• 11. Sakata Y., Hirao Y., Tatemitsu H,, Misumi S., Ochiai H. and Shibata H., Tetrahedron, 45,4717 (1989).