NaIO4-mediated selective oxidation of alkylarenes and benzylic bromides/alcohols to carbonyl derivatives using water as solvent

Journal of Organic Chemistry

Volumn 71, Issue 13, 2006, Pages 5043-5046

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

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CARBOXYLIC ACIDS; DERIVATIVES; REACTION KINETICS; SODIUM COMPOUNDS; SOLVENTS; TOLUENE;

BENZYLIC ALCOHOLS; BENZYLIC BROMIDES; METHYLARENES; REACTION CONDITIONS;

ORGANIC COMPOUNDS;

4 BROMOBENZOIC ACID; ALDEHYDE; BENZOIC ACID DERIVATIVE; BENZYL ALCOHOL; BENZYL BROMIDE; BROMINE; CARBONYL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; PERIODATE SODIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SOLVENT; TOLUENE; TRANSITION ELEMENT; UNCLASSIFIED DRUG; WATER; ALCOHOL DERIVATIVE; BENZENE DERIVATIVE; BENZYL DERIVATIVE; BROMIDE; KETONE; PERIODATE; PERIODIC ACID;

ARTICLE; BROMINATION; OXIDATION; QUANTUM YIELD; REACTION ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; BENZENE DERIVATIVES; BENZYL COMPOUNDS; BROMIDES; KETONES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PERIODIC ACID; SOLVENTS; STEREOISOMERISM; WATER;

EID: 33745462569     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0606305     Document Type: Article

References (55)

1. (a) Sheldon, R. A.; Kochi, J. K. Metal Catalyzed Oxidations of Organic Compounds; Academic press: New York, 1981.
2. (b) Cainelli, G.; Cardillo, G. Chromium Oxidations in organic Chemistry; Springer: Berlin, 1984.
3. (c) Hudlicky, M. Oxidations in Organic Chemistry; American Chemical Society: Washington, DC, 1990.
4. (a) Wiberg, K. B. In Oxidation in Organic Chemistry; Wiberg, K. B., Ed; Academic: New York, 1965; Part A, p 69.
5. th ed.; John Wiley & sons: New York, 1992.
6. 4 oxidation, see: Sam, D. J.; Simmons, H. E. J. Am. Chem. Soc. 1972, 94, 4024.
7. 7 oxidation, see: Friedman, L.; Fishel, D. L.; Shechter, H. J. Org. Chem. 1965, 30, 1453.
8. 3 oxidation, see: (i) Muzart, J. Tetrahedron Lett. 1986, 27, 3139.
9. (ii) Muzart, J. Tetrahedron Lett. 1987, 28, 2131.
10. (iii) Yamazaki, S. Org. Lett. 1999, 1, 2129.
11. Sasson, Y.; Zappi, G. D.; Neumann, R. J. Org. Chem. 1986, 51, 2880.
12. Saha, B.; Espenson, J. H. J. Mol. Catal. A: Chem. 2005, 241, 33 and the references therein.
13. Bonvin, Y.; Callens, E.; Larrosa, I.; Henderson, D. A.; Oldham, J.; Burton, A. J.; Barrett, A. G. M. Org. Lett. 2005, 7, 4549.
14. Srinivasan, B.; Changli, S. B. Indian Chem. J. 1971, 5, 33.
15. (a) Dewkar, G. K.; Narina, S. V.; Sudalai, A. Org. Lett. 2003, 5, 4501.
16. (b) Shaikh, T. M.; Sudalai, A. Tetrahedron Lett. 2005, 46, 5589.
17. (c) Emmanuvel, L.; Shaikh, T. M.; Sudalai, A. Org. Lett. 2005, 7, 5071.
18. (a) Moriarty, R. M.; Prakash, I.; Penmasta, R. J. Chem. Soc., Chem. Commun. 1987, 202.
19. (b) Zevaco, T.; Duriach, E.; Postel, M. Tetrahedron Lett. 1993, 34, 2601.
20. (c) Gurunath, S.; Sudalai, A. Synlett 1999, 5, 559.
21. (d) Kameda, K.; Morimoto, K.; Imanaka, T. Chem. Lett. 1988, 1295.
22. (e) Santaniello, E.; Manzocchi, A.; Farachi, C. Synthesis 1980, 563.
23. (f) Ayres, D. C. J. Chem. Soc., Chem. Commun. 1975, 440.
24. (a) Comprehensive Organic Transformations: A Guide to Functional Group Preparations; Larock, R. C., Ed.; Wiley-VCH: New York, 1989.
25. (b) Fisher, C. H. J. Am. Chem. Soc. 1934, 56, 2056.
26. (c) Kornblum, N.; Jones, W. J.; Andersen, G. J. J. Am. Chem. Soc. 1959, 81, 4113.
27. (d) Suzuki, S.; Onishi, T.; Fujita, Y.; Misawa, H.; Otetra, J. Bull. Chem. Soc. Jpn. 1986, 59, 3287.
28. (e) Das, S.; Panigrahi, A. K.; Maikap, G. C. Tetrahedron Lett. 2003, 44, 1375.
29. Itoh, A.; Kodama, T.; Inagaki, S.; Masaki, Y. Org. Lett. 2000, 2, 2455.
30. Backvall, J.-E.; Chowdhury, R. L.; Karlsson, U. J. Chem. Soc., Chem. Commun. 1991, 473.
31. (b) Almeida, M. L. S.; Beller, M.; Wang, G.-Z.; Backvall, J.-E. Chem.-Eur. J. 1996, 2, 1533.
32. (c) Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Brown, S. M.; Urch, C. J. Science 1996, 274, 2044.
33. (d) Arterburn, J. B.; Perry, M. C.; Nelson, S. L.; Dible, B. R.; Holguin, M. S. J. Am. Chem. Soc. 1997, 119, 9309.
34. (e) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2000, 122, 7144.
35. (f) Yamaguchi, K.; Mizuno, N. New. J. Chem. 2002, 26, 972.
36. (g) Muldoon, J.; Brown, S. N. Org. Lett. 2002, 4, 1043.
37. (h) Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766.
38. (i) Zhan, B.-Z.; White, M. A.; Sham, T.-K.; Pincock, J. A.; Doucet, R. J.; Rao, K. V. R.; Robertson, K. N.; Cameron, T. S. J. Am. Chem. Soc. 2003, 125, 2195.
39. (j) Velusamy, S.; Punniyamurthy, T. Org. Lett. 2004, 6, 217.
40. (k) Jiang, N.; Ragauskas, A. J. Org. Lett. 2005, 7, 3689.
41. (a) Varvolgis, A. Hypervalent Iodine in Organic Synthesis; Academic Press: London, 1997.
42. (b) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
43. (c) Marx, M.; Tidwell, T. T. J. Org. Chem. 1984, 49, 788.
44. (d) Tidwell, T. T. Synthesis 1990, 857.
45. (e) Nicolao, K. C.; Baran, P. S.; Zhong, Y.-L. J. Am. Chem. Soc. 2001, 123, 3183.
46. (f) Surendra, K.; Krishnaveni, N. S.; Reddy, M. A.; Nageswar, Y. V. D.; Rao, K. R. J. Org. Chem. 2003, 68, 2058.
47. (g) De Luca, L.; Giacomelli, G.; Porcheddu, A. J. Org. Chem. 2001, 66, 7907.
48. (h) More, J. D.; Finney, N. S. Org. Lett. 2002, 4, 3001.
49. (i) Kuhakarn, C.; Kittigowittana, K.; Pohmakotr, M.; Reutrakul, V. Tetrahedron 2005, 61, 8995.
50. (a) Blair, L. K.; Baldwin, J.; Smith, W. C., Jr. J. Org. Chem. 1977, 42, 1816.
51. (b) Einhorn, J.; Einhorn, C.; Ratajczak, F.; Pierre, J.-L. J. Org. Chem. 1996, 61, 7452.
52. (c) Gogoi, P.; Sarmah, G. K.; Konwar, D. J. Org. Chem. 2004, 69, 5153.
53. (a) Bergman, J.; Engman, L. J. Org. Chem. 1982, 47, 5191.
54. (b) Mestres, R.; Palenzuela, J. Green Chem. 2002, 4, 314.
55. Amati, A.; Dosualdo, G.; Zhao, L.; Bravo, A.; Fontana, F.; Minisci, F.; Bjorsvik, H. R. Org. Process Res. Dev. 1998, 2, 261.