Development of biomimetic catalytic oxidation methods and non-salt methods using transition metal-based acid and base ambiphilic catalysts

Proceedings of the Japan Academy Series B: Physical and Biological Sciences

Volumn 87, Issue 5, 2011, Pages 242-253

  Murahashi, Shun Ichi ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Biomimetic oxidation; Flavin catalyst; Oxidation of amines; Ruthenium catalyst; Sp3 C H activation; Transition metal based acid and base ambiphilic catalyst

Indexed keywords

ACID; ALKALI; INORGANIC SALT; TRANSITION ELEMENT;

BIOMIMETICS; CATALYSIS; CHEMISTRY; METHODOLOGY; OXIDATION REDUCTION REACTION; REVIEW;

ACIDS; ALKALIES; BIOMIMETICS; CATALYSIS; OXIDATION-REDUCTION; SALTS; TRANSITION ELEMENTS;

EID: 79957562545     PISSN: 03862208     EISSN: 13492896     Source Type: Journal    
DOI: 10.2183/pjab.87.242     Document Type: Review

References (60)

1. Murahashi, S.-I. (1992) Biomimetic oxidation in organic synthesis using transition metal catalysts. Pure Appl. Chem. 64, 403-412
2. Murahashi, S.-I. (1995) Synthetic aspects of metal-catalyzed oxidations of amines and related reactions. Angew. Chem. Int. Ed. Engl. 34, 2443-2465
3. Murahashi, S.-I. and Zhang, D. (2008) Ruthenium catalyzed biomimetic oxidation in organic synthesis inspired by cytochrome P-450. Chem. Soc. Rev. 37, 1490-1501.
4. Murahashi, S.-I., Naota, T. and Yonemura, K. (1988) Ruthenium-catalysed cytochrome P-450 type oxidation of tertiary amines with alkyl hydroperoxides. J. Am. Chem. Soc. 110, 8256-8258.
5. Murahashi, S.-I., Naota, T., Miyaguchi, N. and Nakato, T. (1992) Ruthenium-catalyzed oxidation of tertiary amines with hydrogen peroxide in the presence of methanol. Tetrahedron Lett. 33, 6991- 6994.
6. Murahashi, S.-I., Naota, T. and Taki, H. (1985) Ruthenium-catalyzed oxidation of secondary amines to imines using t-butyl hydroperoxide. J. Chem. Soc. Chem. Commun. 613-614.
7. Murahashi, S.-I., Okano, Y., Sato, H., Nakae, T. and Komiya, N. (2007) Aerobic ruthenium-catalyzed oxidative transformation of secondary amines to imines. Synlett 1675-1678.
8. Murahashi, S.-I., Naota, T., Kuwabara, T., Saito, T., Kumobayashi, H. and Akutagawa, S. (1990) Ruthenium-catalyzed oxidation of amides and lactams with peroxides. J. Am. Chem. Soc. 112, 7820-7822.
9. Naota, T., Nakato, T. and Murahashi, S.-I. (1990) Novel method for,-substitution of amines via N-methoxycarbonyl-α-t-butyldioxyamines. Tetrahedron Lett. 31, 7475-7478.
10. Murahashi, S.-I., Mitani, A. and Kitao, K. (2000) Ruthenium catalyzed glycine-selective oxidative backbone modification of peptides. Tetrahedron Lett. 41, 10246-10249.
11. Murahashi, S.-I., Saito, T., Naota, T., Kumobayashi, H. and Akutagawa, S. (1991) Ruthenium-catalyzed oxidation of β-lactams with molecular oxygen and aldehydes. Tetrahedron Lett. 32, 5991- 5994.
12. Murahashi, S.-I., Komiya, N., Terai, H. and Nakae, T. (2003) Aerobic ruthenium-catalyzed oxidative cyanation of tertiary amines with sodium cyanide. J. Am. Chem. Soc. 125, 15312-15313
13. Murahashi, S.-I., Komiya, N. and Terai, H. (2005) Ruthenium-catalyzed oxidative cyanation of tertiary amines with hydrogen peroxide and sodium cyanide. Angew. Chem. Int. Ed. 44, 6931-6933
14. Murahashi, S.-I., Nakae, T., Terai, H. and Komiya, N. (2008) Ruthenium-catalyzed oxidative cyanation of tertiary amines with molecular oxygen or hydrogen peroxide and sodium cyanide: sp3 C-H bond activation and carbon-carbon bond formation. J. Am. Chem. Soc. 130, 11005-11012.
15. Murahashi, S.-I., Saito, T., Hanaoka, H., Murakami, Y., Naota, T., Kumobayashi, H. and Akutagawa, S. (1993) Ruthenium-catalyzed oxidative transformation of alkenes to,α-ketols with peracetic acid. Simple synthesis of Cortisone acetate. J. Org. Chem. 58, 2929-2930.
16. Murahashi, S.-I., Naota, T. and Hanaoka, H. (1993) Osmium-catalyzed oxidative transformation of alkenes to,α-ketols with peracetic acid. Chem. Lett. 1767-1770.
17. Hotopp, T., Gutke, H.-J. and Murahashi, S.-I. (2001) Synthesis of 4-demethoxyadriamycinone utilizing ruthenium-catalyzed oxidation of allyl acetates. Tetrahedron Lett. 42, 3343-3346.
18. Murahashi, S.-I., Naota, T., Miyaguchi, N. and Noda, S. (1996) Ruthenium-catalyzed oxidation of phenols with alkyl hydroperoxides. A novel, facile route to 2-substituted quinones. J. Am. Chem. Soc. 118, 2509-2510.
19. Murahashi, S.-I., Komiya, N., Oda, Y., Kuwabara, T. and Naota, T. (2000) Ruthenium-catalyzed oxidation of alkanes with tert-butyl hydroperoxide and peracetic acid. J. Org. Chem. 65, 9186-9193.
20. Komiya, N., Noji, S. and Murahashi, S.-I. (2001) Ruthenium-catalyzed oxidation of alkanes with peracetic acid in trifluoroacetic acid: Ruthenium as an efficient catalyst for the oxidation of unactivated C-H bonds. Chem. Commun. (Camb.), 65-66.
21. Murahashi, S.-I., Oda, Y. and Naota, T. (1992) Ironand ruthenium-catalyzed oxidations of alkanes with molecular oxygen in the presence of aldehydes and acids. J. Am. Chem. Soc. 114, 7913-7914.
22. Murahashi, S.-I., Naota, T. and Komiya, N. (1995) Metalloporphyrin-catalyzed oxidation of alkanes with molecular oxygen in the presence of acetaldehyde. Tetrahedron Lett. 36, 8059-8062.
23. Komiya, N., Naota, T., Oda, Y. and Murahashi, S.-I. (1997) Aerobic oxidation of alkanes and alkenes in the presence of aldehydes catalyzed by copper salts and copper-crown ether. J. Mol. Catal. 117, 21-35.
24. Murahashi, S.-I., Komiya, N., Hayashi, Y. and Kumano, T. (2001) Copper complexes for catalytic, aerobic oxidation of hydrocarbons. Pure Appl. Chem. 73, 311-314.
25. Murahashi, S.-I., Oda, T. and Masui, Y. (1989) Flavin-catalyzed oxidation of amines and sulfur compounds with hydrogen peroxide. J. Am. Chem. Soc. 111, 5002-5003.
26. Murahashi, S.-I., Ono, S. and Imada, Y. (2002) Asymmetric Baeyer-Villiger reaction with hydrogen peroxide catalyzed by a novel planar-chiral bisflavin. Angew. Chem. Int. Ed. 41, 2366-2368.
27. Imada, Y., Iida, H., Ono, S. and Murahashi, S.-I. (2003) Flavin catalyzed oxidations of sulfides and amines with molecular oxygen. J. Am. Chem. Soc. 125, 2868-2869.
28. Imada, Y., Iida, H., Ono, S., Masui, Y. and Murahashi, S.-I. (2006) Flavin-catalyzed oxidation of amines and sulfides with molecular oxygene: Biomimetic green oxidation. Chem. Asian J. 1, 136-147.
29. Iida, H., Imada, Y., Murahashi, S.-I. and Naota, T. (2005) An aerobic, organocatalytic, and chemoselective method for Baeyer-Villiger oxidation. Angew. Chem. Int. Ed. 44, 1704-1706.
30. Murahashi, S.-I., Mitsui, H., Shiota, T., Tsuda, T. and Watanabe, S. (1990) Tungstate-catalyzed oxidation of secondary amines to nitrones.,-substitution of secondary amines via nitrones. J. Org. Chem. 55, 1736-1744
31. Murahashi, S.-I., Shiota, T. and Imada, Y. (1992) Oxidation of secondary amines to nitrones. 6-methyl-2,3,4,5-tetrahydropyridine N-oxide. Org. Synth. 70, 265- 271.
32. Murahashi, S.-I. and Shiota, T. (1987) Selenium dioxide catalyzed oxidation of secondary amines with hydrogen peroxide. Simple synthesis of nitrones from secondary amines. Tetrahedron Lett. 28, 2383-2386.
33. Murahashi, S.-I., Imada, Y. and Ohtake, H. (1994) Tungstate-catalyzed decarboxylative oxidation of N-alkyl-α-amino acids: An efficient method for regioselective synthesis of nitrones. J. Org. Chem. 59, 6170-6172.
34. Murahashi, S.-I., Tsuji, T. and Ito, S. (2000) Synthesis of optically active N-hydroxylamines by asymmetric hydrogenation of nitrones with iridium catalysts. Chem. Commun. (Camb.), 409-410.
35. Ohtake, H., Imada, Y. and Murahashi, S.-I. (1999) Highly diastereoselective addition of a chiral ketene silyl acetal to nitrones: Asymmetric synthesis of β-amino acids and key intermediates of Olactam antibiotics. J. Org. Chem. 64, 3790-3791
36. Kawakami, T., Ohtake, H., Arakawa, H., Okachi, T., Imada, Y. and Murahashi, S.-I. (1999) Asymmetric synthesis of β-amino acids by addition of chiral enolates to N-acyloxyiminium ions and application for synthesis of optically active 5-substituted 8-methylindolizidines. Org. Lett. 1, 107-110
37. Ohtake, H., Imada, Y. and Murahashi, S.-I. (1999) Regioselective synthesis of nitrones by decarboxylative oxidation of N-alkyl-α-amino acids and application to the synthesis of 1-azabicyclic. Bull. Chem. Soc. Jpn. 72, 2737- 2754
38. Kawakami, T., Ohtake, H., Arakawa, H., Okachi, T., Imada, Y. and Murahashi, S.-I. (2000) Asymmetric synthesis of β-amio acids by addition of chiral enolates to nitrones via N-acyloxyiminium ions. Bull. Chem. Soc. Jpn. 73, 2423-2444.
39. Murahashi, S.-I., Imada, Y., Kawakami, T., Harada, K., Yonemushi, Y. and Tomita, N. (2002) Enantioselective addition of ketene silyl acetals to nitrones catalyzed by chiral titanium complexes. Synthesis of optically active β-amino acids. J. Am. Chem. Soc. 124, 2888-2889.
40. Murahashi, S.-I. and Naota, T. (1996) A new way for efficient catalysis by using low valent ruthenium complexes as redox Lewis acid and base catalysts. Bull. Chem. Soc. Jpn. 69, 1805-1824
41. Naota, T., Takaya, H. and Murahashi, S.-I. (1998) Ruthenium-catalyzed reactions for organic synthesis. Chem. Rev. 98, 2599-2660
42. Murahashi, S.-I. and Takaya, H. (2000) Low-valent ruthenium and iridium hydride complexes as alternatives to Lewis acid and base catalysts. Acc. Chem. Res. 33, 225-233.
43. Murahashi, S.-I., Hirano, T. and Yano, T. (1978) Palladium catalyzed amine exchange reaction of tertiary amines. Insertion of palladium(0) into carbon-hydrogen bonds. J. Am. Chem. Soc. 100, 348-350.
44. Murahashi, S.-I. and Watanabe, T. (1979) Palladium catalyzed hydrolysis of tertiary amines with water. J. Am. Chem. Soc. 101, 7429-7430.
45. Yoshimura, N., Moritani, I., Shimamura, T. and Murahashi, S.-I. (1973) Synthesis of unsymmetrical secondary and tertiary amines from amines by palladium catalyst. J. Am. Chem. Soc. 95, 3038- 3039
46. Murahashi, S.-I., Yoshimura, N., Tsumiyama, T. and Kojima, T. (1983) Catalytic alkyl group exchange reaction of primary and secondary amines. J. Am. Chem. Soc. 105, 5002- 5011.
47. Naota, T., Taki, H., Mizuno, M. and Murahashi, S.-I. (1989) Ruthenium-catalyzed Aldol and Michael reactions of activated nitriles. J. Am. Chem. Soc. 111, 5954-5955.
48. Murahashi, S.-I., Naota, T., Taki, H., Mizuno, M., Takaya, H., Komiya, S., Mizuho, Y., Oyasato, N., Hiraoka, M., Hirano, M. and Fukuoka, A. (1995) Ruthenium-catalyzed Aldol and Michael reactions of nitriles. Carbon-carbon bond formation by,-C-H activation of nitriles. J. Am. Chem. Soc. 117, 12436-12451.
49. Naota, T., Tanna, A. and Murahashi, S.-I. (2000) Synthesis and characterization of C- and N-bound isomers of transition metal α-cyanocarbanions. J. Am. Chem. Soc. 122, 2960-2961
50. Naota, T., Tanna, A., Kamuro, S. and Murahashi, S.-I. (2002) Mechanism of the interconversions between Cand N-bound transition metalα-cyanocarbanions. J. Am. Chem. Soc. 124, 6842-6843.
51. Murahashi, S.-I., Naota, T. and Nakano, Y. (2009) Ruthenium-catalyzed regioselective reactions of nitriles and 1,3-dicarbonyl compounds with terminal alkynes. Synlett 3355-3360.
52. Takaya, H., Naota, T. and Murahashi, S.-I. (1998) Iridium hydride complex catalyzed addition of nitriles to carbon-nitrogen triple bonds of nitriles. J. Am. Chem. Soc. 120, 4244-4245.
53. Takaya, H., Kojima, S. and Murahashi, S.-I. (2001) Rhodium complex-catalyzed reaction of isonitriles with carbonyl compounds: Catalytic synthesis of pyrroles. Org. Lett. 3, 421-424.
54. Takaya, H., Ito, M. and Murahashi, S.-I. (2009) Rhenium-catalyzed addition of carbonyl compounds to the carbon-nytrogen triple bonds of nitriles:α-C-H activation of carbonyl compounds. J. Am. Chem. Soc. 131, 10824-10825.
55. 3-H bond activationα to the trifluoromethyl group. Angew. Chem. Int. Ed. 48, 2047-2049.
56. Murahashi, S.-I., Sasao, S., Saito, E. and Naota, T. (1992) Ruthenium-catalyzed hydration of nitriles and transformation of α-keto nitriles to enelactams. J. Org. Chem. 57, 2521-2523.
57. Naota, T., Shichijo, Y. and Murahashi, S.-I. (1994) Ruthenium complex catalyzed condensation of nitriles with alcohols. J. Chem. Soc. Chem. Commun. 1359-1360.
58. Murahashi, S.-I., Naota, T., Ito, K., Maeda, Y. and Taki, H. (1987) Ruthenium-catalyzed oxidative transformation of alcohols and aldehydes to esters and lactones. J. Org. Chem. 52, 4319-4327.
59. Murahashi, S.-I., Naota, T. and Saito, E. (1986) Ruthenium-catalyzed amidation of nitriles with amines. A novel, facile route to amides and polyamides. J. Am. Chem. Soc. 108, 7846-7847.
60. Takaya, H., Yoshida, K., Isozaki, K., Terai, H. and Murahashi, S.-I. (2003) Transition-metal-based Lewis acid and base ambiphilic catalysts of iridium hydride complexes: Multicomponent synthesis of glutarimides. Angew. Chem. Int. Ed. 42, 3302- 3304.