NaIO4/LiBr-mediated direct conversion of benzylic alcohols and aromatic aldehydes to aromatic esters

Synthetic Communications

Volumn 37, Issue 16, 2007, Pages 2641-2646

  Shaikh, Tanveer Mohammad Ali ^a   Emmanuvel, Lourdusamy ^a   Sudalai, Arumugam ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Aromatic ester; Benazaldehyde; Benzyl alcohol; Lithium bromide; Sodium metaperiodate

Indexed keywords

ALCOHOL; ALDEHYDE; BENZALDEHYDE DERIVATIVE; BENZYL ALCOHOL; ESTER DERIVATIVE; LITHIUM BROMIDE; LITHIUM DERIVATIVE; METHANOL; PERIODATE SODIUM; UNCLASSIFIED DRUG;

ARTICLE; ESTERIFICATION; OXIDATION;

EID: 34547956821     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701465032     Document Type: Article

References (28)

1. (a) Corey, E. J.; Gilman, N. W.; Ganem, B. E. J. Am. Chem. Soc. 1968, 90, 5616;
2. (b) Sundararaman, P.; Walker, E. C.; Djerassi, C. Tetrahedron Lett. 1978, 19, 1627;
3. (c) Garegg, P. J.; Olsson, L.; Oscarson, S. J. Org. Chem. 1995, 60, 2200;
4. (d) Ogawa, T.; Matsui, M. J. Am. Chem. Soc. 1976, 98, 1629.
5. (a) Gopinath, R.; Patel, B. K. Org. Lett. 2000, 2, 577;
6. (b) Gopinath, R.; Paital, A. R.; Patel, B. K. Tetrahedron Lett. 2002, 43, 5123;
7. (c) Gopinath, R.; Barkakaty, B.; Talukdar, B.; Patel, B. K. J. Org. Chem. 2003, 68, 2944.
8. Travis, B. R.; Sivakumar, M.; Hollist, G. O.; Borhan, B. Org. Lett. 2003, 5, 1031.
9. Wuts, P. G. M.; Bergh, C. L. Tetrahedron Lett. 1986, 27, 3995.
10. William, D. R.; Klingler, F. D.; Allen, E. E.; Lichtenthaler, F. W. Tetrahedron Lett. 1988, 29, 5087.
11. Sundararaman, P.; Walker, E. C.; Djerassi, C. Tetrahedron Lett. 1978, 19, 1627.
12. Sayama, S.; Onami, T. Synlett. 2004, 2739.
13. O'Connor, B.; Just, G. Tetrahedron Lett. 1987, 28, 3235.
14. Okimoto, M.; Chiba, T. J. Org. Chem. 1988, 53, 218.
15. Marko, I. E.; Mekhalfia, A.; Ollis, W. D. Synlett. 1990, 347.
16. Qian, G.; Zhao, R.; Ji, D.; Lu, G.; Qi, Y.; Suo, J. Chem. Lett. 2004, 33, 834.
17. Victor Paul Raj, I.; Sudalai, A. Tetrahedron Lett. 2005, 46, 8303.
18. Schulze, A.; Pagona, G.; Giannis, A. Synth. Commun. 2006, 36, 1147.
19. McDonald, C. E.; Nice, L. E.; Shaw, A. W.; Nestor, N. B. Tetrahedron Lett. 1993, 34, 2741.
20. Takase, K.; Masuda, H.; Kai, O.; Nishiyama, Y.; Sakaguchi, S.; Ishii, Y. Chem. Lett. 1995, 34, 871.
21. Kageyama, T.; Kawahara, S.; Kitamura, K.; Ueno, Y.; Okawara, M. Chem. Lett. 1983, 1097.
22. Wang, N.; Liu, R.; Xu, Q.; Liang, X. Chem. Lett. 2006, 35, 566.
23. Amati, A.; Dosualdo, G.; Zhao, L.; Bravo, A.; Fontana, F.; Minisci, F.; Bjorsvik, H. R. Org. Process Res. Dev. 1998, 2, 261.
24. (a) Dewkar, G. K.; Narina, S. V.; Sudalai, A. Org. Lett. 2003, 5, 4501;
25. (b) Shaikh, T. M. A.; Sudalai, A. Tetrahedron Lett. 2005, 46, 5589;
26. (c) Emmanuvel, L.; Shaikh, T. M. A.; Sudalai, A. Org. Lett. 2005, 7, 5071;
27. (d) Emmanuvel, L.; Shukla, R. K.; Gurunath, S.; Sivaram, S.; Sudalai, A. Tetrahedron Lett. 2006, 47, 4793-4796;
28. (e) Shaikh, T. M. A.; Emmanuvel, L.; Sudalai, A. J. Org. Chem. 2006, 71, 5043-5046.