Wacker oxidation of alkenes using a fluorous biphasic system. A mild preparation of polyfunctional ketones

Tetrahedron Letters

Volumn 39, Issue 37, 1998, Pages 6667-6670

  Betzemeier, Bodo ^a   Lhermitte, Frédéric ^a   Knochel, Paul ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BENZENE DERIVATIVE; KETONE DERIVATIVE; POLYFUNCTIONAL GROUP;

ARTICLE; CATALYSIS; CHEMICAL REACTION; OXIDATION;

EID: 0032505207     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01355-0     Document Type: Article

References (16)

1. 1. (a) Klement, I.; Lütjens, H.; Knochel, P. Angew. Chem. Int. Ed. Engl. 1997, 36, 1496;
2. (b) Pozzi, G.; Banfi, S.; Manfredi, A.; Montanari, F.; Quici, S. Tetrahedron 1996, 52, 11879.
3. 2. (a) Horvárth, I. T.; Rábai, J. Science 1994, 266, 72;
4. (b) Curran, D. P. Chemtracts Org. Chem. 1996, 9, 75;
5. (c) Cornils, B. Angew. Chem. Int. Ed. Engl. 1997, 36, 2057.
6. 3. Betzemeier, B.; Knochel, P. Angew. Chem. Int. Ed. Engl. 1997, 36, 2623.
7. 4. (a) Tsuji, J. Synthesis 1984, 369;
8. (b) Tsuji, J; Nagashima, H; Hori, K. Chem. Lett. 1980, 257;
9. (c) Roussel, M.; Mimoun, H. J. Org. Chem. 1980, 45, 5387.
10. 5. For another oxidation in fluorous biphasic systems using t-BuOOH: Vincent, J.-M.; Rabion, A.; Yachandra, V. K.; Fish, R. H. Angew. Chem. Int. Ed. Engl. 1997, 36, 2346.
11. 8, 75 MHz): δ = 179.4 (t, J = 23 Hz), 120.0-108.7 (m), 92.8 (s).
12. 7. Spectroscopic data was consistent with commercially available material.
13. 3, 75 MHz): δ = 209.1, 178.5, 64.3, 43.7, 38.6, 29.8, 29.2, 29.1, 28.5, 27.1, 25.9, 23.8.
14. 9. For Spectroscopic data see: (a) Bach, T. Liebigs Ann. 1995, 855;
15. (b) Schulz, S.; Toft S. Tetrahedron 1993, 49, 6805.
16. 4) and evaporation of the solvents, the crude oil was purified by flash chromatography (pentane:ether 9:1) yielding pure 4-methoxyacetophenone (2e: 114 mg, 76 % yield) as a colorless solid.