Development of manganese(III) acetate along with schiff-base ligands as the catalyst for the oxygenation of olefins in the O2/NaBH4 system

Bulletin of the Korean Chemical Society

Volumn 25, Issue 10, 2004, Pages 1455-1456

  Lee, Nam Ho ^a   Baik, Jong Seok ^a   Han, Sung Bin ^a  

^a Jeju National University   (South Korea)

Author keywords

Manganese acetate; Molecular oxygen; Oxidation; Schiff base; Sodium borohydride

Indexed keywords

ACETIC ACID; ALKENE; BORATE SODIUM; MANGANESE ACETATE; MANGANESE DERIVATIVE; ORGANIC SOLVENT; OXYGEN; SCHIFF BASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; COMPLEX FORMATION; ELECTRON; GAS CHROMATOGRAPHY; OXIDATION; OXYGENATION; REACTION ANALYSIS;

EID: 10644262142     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2004.25.10.1455     Document Type: Article

References (14)

1. For reviews, see (a) Simándi, L. I. Catalytic Activation of Dioxygen by Metal Complexes; Kluwer Academic Publishers: Boston, 1992.
2. (b) Mukaiyama, T.; Yamada, T. Bull. Chem. Soc. Jpn. 1995, 68, 17.
3. (c) Baiker, A. Chem. Rev. 2004, 104, 3037.
4. For selected recent examples, see (a) Marko, I.; Giles, P. R.; Tsukazaki, M.; Brown, S. M.; Urch, C. J. Science 1996, 274, 2044.
5. (b) Magnus, P.; Payne, A. H.; Waring, M. J.; Scott, D. A.; Lynch, V. Tetrahedron Lett. 2000, 41, 9725.
6. (c) Tokuyasu, T.; Kunikawa, S.; Abe, M.; Masuyama, A.; Nojima, M.; Kim, H.-S.; Begum, K.; Wataya, Y. J. Org. Chem. 2003, 68, 7361.
7. (d) Choi, E.-J.; Lee, C.-M.; Chang, S.-B. Org. Lett. 2002, 4, 2369.
8. Lee, N. H.; Baik, J. S.; Han, S.-B. Bull. Korean Chem. Soc. 1999, 20, 867.
9. Lee, N. H.; Byun, J. C.; Baik, J. S.; Han, C.-H.; Han, S.-B. Bull. Korean Chem. Soc. 2002, 23, 1365.
10. Examination of manganese(II) acetate with a nitrogen in the analogous olefin oxygenation has been reported to give low yield (< 40%). See, Hirao, T.; Mikami, S.; Ohshiro, Y. Synlett. 1990, 541.
11. Synthesis and isolation of the LMn(III)Cl (L = 3) complex could not be achieved.
12. 4 (2 mmol, 78 mg) dissolved in 4 mL ethanol over 20 min, and the mixture was stirred for 4 hrs. After typical work-up, 2-phenyl-2-propanol (2b, 106 mg, 78% yield) was obtained as the product.
13. For the mechanistic studies on analogous metalloporphyrin-catalyzed olefin oxygenation, see (a) Takeuchi, M.; Kano, K. Bull. Chem. Soc. Jpn. 1994, 67, 1726.
14. (b) Takeuchi, M.; Koreda, M.; Kano, K.; Yoshida, Z-I. J. Mol. Catal. 1996, 113, 51.