Cobalt(II)-catalyzed oxidation of alcohols into carboxylic acids and ketones with hydrogen peroxide

Tetrahedron Letters

Volumn 44, Issue 32, 2003, Pages 6033-6035

  Das, Subhabrata ^a   Punniyamurthy, T ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

Alcohols; Catalyst; Cobalt(II) complex; Hydrogen peroxide; Oxidation

Indexed keywords

ALCOHOL DERIVATIVE; ALKANOL; CARBOXYLIC ACID DERIVATIVE; COBALT; HYDROGEN PEROXIDE; KETONE DERIVATIVE;

ALCOHOL OXIDATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; INFRARED RADIATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REDUCTION;

EID: 0038305256     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01479-5     Document Type: Article

References (16)

1. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Ley, S. V., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, pp. 251-325.
2. Marko I.E., Giles P.R., Tsukazaki M., Chelle-Regnaut I., Gautier A., Brown S.M., Urch C.J. J. Org. Chem. 64:1999;2433.
3. Dijksman A., Arends I.W.C.E., Sheldon R.A. Synlett. 2001;102.
4. Betzemeier B., Cavazzini M., Quici S., Knochel P. Tetrahedron Lett. 41:2000;4343.
5. Coleman K.S., Coppe M., Thomas C., Osborn J.A. Tetrahedron Lett. 40:1999;3723.
6. Wang Y., DuBois J.L., Hedman B., Hodgson K.O., Stack T.D.P. Science. 279:1998;537.
7. Saint-Aman E., Menage S., Pierre J.D., Defrancq E., Gellon G. New. J. Chem. 1998;393.
8. Chaudhuri P., Hess M., Muller J., Hildenbrand K., Bill E., Weyhermuller T., Wieghardt K. J. Am. Chem. Soc. 121:1999;9599.
9. Zhao M., Li J., Mano E., Song Z., Tschaen D.M., Grabowski E.J.J., Reider P.J. J. Org. Chem. 64:1999;2564.
10. Carlsen P.H.J., Katsuki T., Martin V.S., Sharpless K.B. J. Org. Chem. 46:1981;3936.
11. ten Brink G.-J., Arends I.W.C.E., Sheldon R.A. Science. 287:2000;1637.
12. Miyata A., Murakami M., Irie R., Katsuki T. Tetrahedron Lett. 42:2001;7067.
13. Masutani K., Uchida T., Irie R., Katsuki T. Tetrahdron Lett. 41:2000;5119.
14. Punniyamurthy T., Iqbal J. Tetrahedron Lett. 35:1994;4007.
15. +).
16. 2 (6.8 ml, 60 mmol) was stirred in acetonitrile (5 ml) at ca. 80°C under atmospheric oxygen for the appropriate time (see Table 1). The reaction mixture was then cooled to ambient temperature and dimethyl sulfide (50 μl) was added. After further stirring for 0.5 h at ambient temperature, the aqueous acetonitrile was removed by rotary evaporation under reduced pressure and the residue was passed through a short pad of silica gel using ethyl acetate and hexane to afford the analytically pure carboxylic acid.