The economic synthesis of pyridinium fluorochromate(VI), C 5H5NH[CrO3F] (PFC), and solvent-free oxidation of organic substrates with PFC

Synthetic Communications

Volumn 34, Issue 22, 2004, Pages 4077-4087

  Chaudhuri, Mihir K ^a   Dehury, Sanjay K ^a   Dhar, Siddhartha S ^a   Sinha, Upasana B ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

5 steroid; Deprotection; Oxidations; Pyridinium fluorochromate; Solvent free

Indexed keywords

ALLYL COMPOUND; BENZILIC ACID; BENZOIN; CARBONYL DERIVATIVE; CHROMIC ACID; CRYSTALLIN; CYCLOHEXANONE; KETONE; POLYCYCLIC HYDROCARBON; PYRIDINE; PYRIDINIUM DERIVATIVE; PYRIDINIUM FLUOROCHROMATE; SULFIDE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEPROTECTION REACTION; OXIDATION; STOICHIOMETRY; SYNTHESIS;

EID: 8644268829     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200036584     Document Type: Article

References (37)

1. Fieser, L.F.; Fieser, M. Reagents for Organic Synthesis; John Wiley & Sons: New York, 1967; Vol. 1 and subsequent volumes in the series.
2. Collins, J.C.; Hess, W.W.; Franck, F.J. Dipyridine-chromium(VI) oxide oxidation of alcohols in dichloromethane. Tetrahedron Lett. 1968, (30), 3363.
3. Corey, E.J.; Fleet, G.W.J. Chromium trioxide-3,5-dimethylpyrazole complex as a reagent for oxidation of alcohols to carbonyl compounds. Tetrahedron Lett. 1973, (45), 4499.
4. (a) Corey, E.J.; Suggs, J.W. Pyridinium chlorochromate. Efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds. Tetrahedron Lett. 1975, (31), 2647;
5. (b) Piancatelli, G.; Scettri, A.; D'Auria, M. Pyridinium chlorochromate: a versatile oxidant in organic synthesis. Synthesis 1982, (4), 245.
6. Corey, E.J.; Schmidt, G. Useful procedures for the oxidation of alcohols involving pyridinium dichromate in aprotic media. Tetrahedron Lett. 1979, (5), 399.
7. Guziec, F.S.; Luzzio, F.A. The oxidation of alcohols using 2,2′-bipyridinium chlorochromate. Synthesis 1980, (9), 691.
8. (a) Bhattacharjee, M.N.; Chaudhuri, M.K.; Dasgupta, H.S.; Roy, N.; Khathing, D.T. Pyridinium fluorochromate: a new and efficient oxidant for organic substrates. Synthesis 1982, (7), 588;
9. 3F (PFC), oxidations. Stoichiometry of oxidation of alcohols. Evidence for oxygen transfer, and the identity of the reduced chromium species. Tetrahedron 1987, 43 (22), 5389;
10. 3F]. Inorg. Synth. John Wiley & Sons: New York, 1990; Vol. 27, 310;
11. 3F], and its crystal structure. J. Fluorine Chem. 1997, 81 (2), 211.
12. 3F]: an improved Cr(VI)-oxidant for organic substrates. Bull. Chem. Soc. Jpn 1994, 67 (7), 1894.
13. 3F], (DmpzHFC): a convenient new reagent for oxidation of organic substrates. Tetrahedron 2001, 57 (12), 2445.
14. Nonaka, T.; Kanemoto, S.; Oshima, K.; Nozaki, H. Pyridinium fluorochromate or benzyltrimethylammonium chlorochromate for selective oxidation of alcohols. Bull. Chem. Soc. Jpn 1984, 57 (7), 2019.
15. Banerji, K.K. Kinetics of the oxidation of organic sulfides by pyridinium fluorochromate. J. Chem. Soc. Perkin Trans. 2 1988, (12), 2065.
16. Agarwal, S.; Chowdhury, K.; Banerji, K.K. Kinetics and mechanism of the oxidation of aromatic aldehydes by pyridinium fluorochromate. J. Org. Chem. 1991, 56 (17), 5111.
17. Mata, E.; Setti, E.; Mascaretti, O. Synthesis of analogs of 6β-bromo-penicillanic acid and penicillanic acid S,S-dioxide. Part 1. Synthesis of 3α-derivatives of 6β-bromo-2,2-dimethylpenam and 2,2-dimethylpenam S,S-dioxide. J. Chem. Soc. Perkin Trans. 1 1988, (6), 1551.
18. Parish, E.J.; Sun, H.; Kizito, S.; Boos, T.L. An improved synthesis of 3β-acetoxy-lanost-8-en-24-one (24-ketolanosteryl acetate). Molecules 2000, 5 (1), 114 (see also references cited therein).
19. Ho, T.-L.; Jana, G.H. Desilylative oxidation of alkyl trimethylsilyl ethers with pyridinium fluorochromate. J. Chin. Chem. Soc. 1999, 46 (4), 639.
20. (a) Metzger, J.D. Solvent-free organic syntheses. Angew Chem. Int. Ed. 1998, 37 (21), 2975;
21. (b) Tanaka, K.; Toda, F. Solvent-free organic synthesis. Chem Rev. 2000, 100 (3), 1025;
22. (c) Cave, G.W.V.; Raston, C.L.; Scott, J.L. Recent advances in solventless organic reactions: towards benign synthesis with remarkable versatility. Chem. Commun. 2001, (21), 2159;
23. (d) Rothenberg, G.; Downie, A.P.; Raston, C.L.; Scott, L. Understanding solid/solid organic reactions. J. Am. Chem. Soc. 2001, 123 (36), 8701.
24. (a) Salehi, P.; Firouzabadi, H.; Farrokhi, A.; Ghalizadeh, M. Solvent-free oxidations of alcohols, oximes, aldehydes and cyclic acetals by pyridinium chlorochromate. Synthesis 2001, (15), 2273;
25. (b) Lou, J.-D.; Xu, Z.-N. Selective oxidation of primary alcohols with chromium trioxide under solvent free conditions. Tetrahedron Lett. 2002, 43 (35), 6095;
26. (c) Lou, J.-D.; Xu, Z.-N. Solvent free oxidation of alcohols with manganese dioxide. Tetrahedron Lett. 2002, 43 (35), 6149;
27. (d) Lou, J.-D.; Xu, Z.-N. Selective solvent-free oxidation of alcohols with potassium dichromate. Tetrahedron Lett. 2002, 43 (49), 8843;
28. (e) Martin, S.E.; Garrone, A. Efficient solvent-free iron (III) catalyzed oxidation of alcohols by hydrogen peroxide. Tetrahedron Lett. 2003, 44 (3), 549.
29. Kar, G.; Saikia, A.; Bora, U.; Dehury, S.K.; Chaudhuri, M.K. Synthesis of cetyltrimethylammonium tribromide (CTMATB) and its application in the selective oxidation of sulfides to sulfoxides. Tetrahedron Lett. 2003, 44 (24), 4503.
30. (a) Parish, E.J.; Nanduri, V.B.B.; Kohl, H.H.; Taylor, F.R. Oxysterols: chemical synthesis, biosynthesis and biological activities. Lipids 1986, 21 (1), 27 (see also references cited therein);
31. (b) Smith, L.L. Cholesterol Autooxidation; Plenum: New York, 1981;
32. (c) Taylor, F.R.; Saucier, S.E.; Shown, E.P.; Parish, E.J.; Kandutsch, A.A. Correlation between oxysterol binding to a cytosolic binding protein and potency in the repression of hydroxymethylglutaryl coenzyme A reductase. J. Biol. Chem. 1984, 259 (20), 12382;
33. (d) Sato, Y.; Sonoda, Y.; Morisaki, M.; Ikekawa, H. Oxygenated sterols as inhibitors of enzymic conversion of dihydrolanosterol into cholesterol. Chem. Pharm. Bull. Jpn 1984, 32 (8), 3305;
34. (e) Cheng, K.-P.; Nagano, N.; Bang, L.; Ourisson, G.J. Chemistry and biochemistry of Chinese drugs. Part I. Sterol derivatives cytotoxic to hepatoma cells, isolated from the drug Bombyx cum Botryte. J. Chem. Res. (S) 1977, (9), 217;
35. (f) Nagona, H.; Poyser, J.P.; Cheng, K.-P.; Bang, L.; Ourisson, G.J. Chemistry and biochemistry of Chinese drugs. Part II. Hydroxylated sterols, cytotoxic towards cancerous cells: synthesis and testing. J. Chem. Res. (S) 1977, (9), 218.
36. 5-steroids with pyridinium fluorochromate. J. Chem. Res. (S) 1996, (12), 544.
37. Greene, T.W.; Wuts, P.G.M. Protective Groups in Organic Synthesis, 2nd Ed.; John Wiley & Sons: New York, 1999.