Mild oxidation of alcohols with O-lodoxybenzoic acid (IBX) in ionic liquid 1-butyl-3-methyl-imidazolium chloride and water

Organic Letters

Volumn 5, Issue 18, 2003, Pages 3321-3323

  Liu, Zhi ^a   Chen, Zhen Chu ^a   Zheng, Qin Guo ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1 BUTYL 3 METHYLIMIDAZOLIUM CHLORIDE; 2 IODOBENZOIC ACID; ALCOHOL DERIVATIVE; CHLORINE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; EXTRACTION; OXIDATION; RECYCLING;

EID: 0141521516     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0351549     Document Type: Article

References (28)

1. (a) Varvoglis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: London, 1997.
2. (b) Stang, P. J. J. Org. Chem. 2003, 68, 2997.
3. (c) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
4. (d) Wirth, T.; Hirt, U. H. Synthesis 1999, 1271.
5. (a) Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019.
6. (b) Frigerio, M.; Santagostino, M.; Sputore, S.; Palmisano, G. J. Org. Chem. 1995, 60, 7272.
7. (c) De Munari, S.; Frigerio, M.; Santagastino, M. J. Org. Chem. 1996, 61, 9272. See also ref 3a.
8. IBX has also found use in several other oxidative transformations. For an overview, see: (a) Wirth, T. Angew. Chem., Int. Ed. 2001, 40, 2812. For more recent developments, see: (b) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, W. K.; Kranich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233. (c) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.-L. J. Am. Chem. Soc. 2002, 124, 2245.
9. IBX has also found use in several other oxidative transformations. For an overview, see: (a) Wirth, T. Angew. Chem., Int. Ed. 2001, 40, 2812. For more recent developments, see: (b) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, W. K.; Kranich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233. (c) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.-L. J. Am. Chem. Soc. 2002, 124, 2245.
10. IBX has also found use in several other oxidative transformations. For an overview, see: (a) Wirth, T. Angew. Chem., Int. Ed. 2001, 40, 2812. For more recent developments, see: (b) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Barluenga, S.; Hunt, W. K.; Kranich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233. (c) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.-L. J. Am. Chem. Soc. 2002, 124, 2245.
11. IBX was first prepared over 100 years ago: Hartman, C.; Mayer, V. Chem. Ber. 1893, 26, 1727.
12. Prior to its use as a terminal oxidant in its own right, IBX was identified as a valuable precursor to Dess-Martin Periodinate: Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277 and references therein.
13. (a) Mülbaier, M.; Giannis, A. Angew. Chem., Int. Ed. 2001, 40, 4393.
14. (b) Sorg, G.; Mengel, A.; Jung, G.; Rademan, J. Angew. Chem., Int. Ed. 2001, 40, 4395.
15. (a) More, J. D.; Finney, N. S. Org. Lett. 2002, 4, 3001.
16. (b) Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 2058.
17. (a) Zhao, H.; Malhotra, S. V. Aldrichimica Acta 2002, 35, 75.
18. (b) Dupont, J.; De Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667.
19. (c) Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772.
20. (d) Welton, T. Chem. Rev. 1999, 99, 2071.
21. Huddleston, J. G.; Willauer, H. D.; Swatloski, R. P.; Visser, A. E.; Rogers, R. D. Chem. Commun. 1998, 1765.
22. (a) Xie, Y.-Y.; Chen, Z.-C.; Zheng, Q.-G. Synthesis 2002, 1505.
23. (b) Xie, Y.-Y.; Chen, Z.-C.; Zheng, Q.-G. J. Chem. Res., Synop. 2002, 618.
24. (c) Su, C.; Chen, Z.-C.; Zheng, Q.-G. Synthesis 2003, 555.
25. Alcohols in Table 1 are commercially available and were used as received.
26. Most of the spectral data for the products can be obtained from Sigma-Aldrich via the Internet at http://www.Sigmaaldrich.com. Data for the rest of the products are available in ref 7b.
27. 6) and elemental analysis (>99% purity by HPLC). Ionic liquid [bmim]Cl was recovered by evaporating the filtrate under vacuum to remove water, and more than 95% yield of recovered [bmim]Cl was obtained and reused (containing trace IBX, which did not affect the oxidation at all).
28. Representative Experimental Procedure. To a mixture of [bmim]-Cl (3 mL) and water (0.6 mL) was added IBX (0.31 g, 1.1 mmol). The resulting mixture was stirred at room temperature for 5-10 min, and benzyl alcohol (0.11 g, 1 mmol) was added. The reaction mixture was stirred at room temperature for 5 min, and then the product was extracted with ether (3 × 10 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum to yield 0.11 g (99% yield, > 98% pure by HPLC) of benzaldehyde as a pale yellow liquid.