Sub-stoichiometric oxidation of benzylic alcohols with commercially available activated MnO2 under oxygen atmosphere: A green modification of the benzylic oxidation

Tetrahedron

Volumn 69, Issue 29, 2013, Pages 5968-5972

  Kamimura, Akio ^a   Komatsu, Hiroyuki ^a   Moriyama, Takaaki ^a   Nozaki, Yuichiro ^a  

^a YAMAGUCHI UNIVERSITY GRADUATE SCHOOL OF MEDICINE   (Japan)

Author keywords

Aerobic oxidation; Benzylic oxidation; Green oxidation; Manganese oxide

Indexed keywords

ALDEHYDE; ALLYL ALCOHOL; BENZALDEHYDE; BENZOPHENONE; BENZYL ALCOHOL; MANGANESE DIOXIDE; OXYGEN;

ARTICLE; ATMOSPHERE; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; PRIORITY JOURNAL; STOICHIOMETRY; TEMPERATURE;

EID: 84878879674     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.04.109     Document Type: Article

References (36)

1. S.D. Burke, and R.L. Danheiser Handbook of Reagents for Organic Synthesis, Oxidizing and Reducing Agents 1999 John Wiley and Sons Chichester, UK
2. E.J. Corey, and J.W. Suggs Tetrahedron Lett. 16 1975 2647
3. E.J. Corey, and G. Schmidt Tetrahedron Lett. 20 1979 399
4. A.J. Mancuso, and D. Swern Synthesis 1981 165
5. W.P. Griffith, and S.V. Ley Aldrichimica Acta 23 1990 13
6. S.V. Ley, J. Norman, W.P. Griffith, and S.P. Marsden Synthesis 1994 639
7. D.B. Dess, and J.C. Martin J. Org. Chem. 48 1983 4155
8. R.K. Boeckman Jr., P. Shao, and J.J. Mullins Org. Synth. 77 2000 141
9. T. Vogler, and A. Studer Synthesis 2008 1979
10. G. Piancatelli, and F. Leonelli Org. Synth. 83 2006 18 and references cited therein
11. M. Shibuya, M. Tomizawa, I. Suzuki, and Y. Iwabuchi J. Am. Chem. Soc. 128 2006 8412
12. M. Shibuya, T. Sato, M. Tomizawa, and Y. Iwabuchi Chem. Commun. 2009 1739
13. M. Tomizawa, M. Shibuya, and Y. Iwabuchi Org. Lett. 11 2009 1829
14. M. Shibuya, Y. Sasano, M. Tomizawa, T. Hamada, M. Kozawa, N. Nagahama, and Y. Iwabuchi Synthesis 2011 3418
15. M. Shibuya, Y. Osada, Y. Sasano, M. Tomizawa, and Y. Iwabuchi J. Am. Chem. Soc. 133 2011 6497
16. A.J. Fatiadi Synthesis 1976 65
17. A.J. Fatiadi Synthesis 1976 133
18. J. Attenburrow, A.F.B. Cameron, J.H. Chapman, R.M. Evans, B.A. Hems, A.B.A. Jansen, and T. Walker J. Chem. Soc. 1952 1094
19. O. Mancera, G. Rosenkranz, and F. Sondheimer J. Chem. Soc. 1954 3271
20. A.R. Mattock J. Chem. Res., Synop. 1977 40
21. M. Harfenist, A. Bavley, and W.A. Lazier J. Org. Chem. 19 1954 1608
22. S. Ball, T.W. Goodwin, and R.A. Morton Biochem. J. 42 1948 516
23. L.A. Carpino J. Org. Chem. 35 1970 3971
24. I.M. Goldman J. Org. Chem. 34 1969 1979
25. J.S. Belew, and C. Tek-Ling Chem. Ind. (London) 1967 1958
26. A.J. Fatiadi J. Chem. Soc. B 1971 889
27. 2 is available from Sigma-Aldrich.
28. J. Luo, A. Huang, S.H. Park, S.L. Suib, and C.-L.O. Young Chem. Mater. 10 1998 1561
29. O. Pietro, M. Del Arco, and V. Rives J. Mater. Sci. 38 2003 2815
30. J. Cai, and S.L. Suib Inorg. Chem. Commun. 4 2001 493
31. D. Frias, S. Nousir, I. Barrio, M. Montes, M.A. Centeno, and J.A. Odriozola Mater. Charact. 58 2007 776
32. L.-X. Yang, Y.-J. Zhu, and G.-F. Cheng Mater. Res. Bull. 42 2007 159
33. J. Morales, L. Sanchez, S. Bach, and J.P. Pereira-Ramos Mater. Lett. 56 2002 653
34. Y.-C. Son, V.D. Makwana, A.R. Howell, and S.L. Suib Angew. Chem., Int. Ed. 40 2001 4280
35. A. Kamimura, Y. Nozaki, S. Ishikawa, R. Inoue, and M. Nakayama Tetrahedron Lett. 52 2011 538
36. A. Kamimura, Y. Nozaki, M. Nishiyama, and M. Nakayama RSC Adv. 3 2013 468