Catalytic O-O activation chemistry mediated by iron hangman porphyrins with a wide range of proton-donating abilities

Organic Letters

Volumn 5, Issue 14, 2003, Pages 2421-2424

  Chng, Leng Leng ^a   Chang, Christopher J ^a   Nocera, Daniel G ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALASE; HYDROGEN PEROXIDE; IRON; IRON COMPLEX; OXYGEN; PORPHYRIN; XANTHENE DERIVATIVE; PROTON;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; HYDROGEN BOND; PROTON TRANSPORT; SYNTHESIS; CHEMISTRY; KINETICS;

CATALYSIS; IRON; KINETICS; OXYGEN; PORPHYRINS; PROTONS;

EID: 0141631428     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034581j     Document Type: Article

References (26)

1. Babcock, G. T.; Wikström, M. Nature 1992, 356, 301-309.
2. Tommos, C.; Babcock, G. T. Acc. Chem. Res. 1998, 31, 18-25.
3. Malmström, B. G. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 3.1.3, pp 39-55.
4. Klinman, J. P. Chem. Rev. 1996, 96, 2541-2561.
5. Armstrong, F. A. J. Chem. Soc., Dalton Trans. 2002, 661-671.
6. Sono, M.; Roach, M. P.; Coulter, E. D.; Dawson, J. H. Chem. Rev. 1996, 96, 2841-2887.
7. Deng, T.-j.; Macdonald, I. D. G.; Simianu, M. C.; Sykora, M.; Kincaid, J. R.; Sligar, S. G. J. Am. Chem. Soc. 2001, 123, 269-278.
8. Ozaki, S.-I.; Roach, M. P.; Matsui, T.; Watanbe, Y. Acc. Chem. Res. 2001, 34, 818-825.
9. Chang, C. J.; Brown, J. D. K.; Chang, M. C. Y.; Baker, E. A.; Nocera, D. G. In Electron Transfer in Chemistry; Balzani, V., Ed.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 3.2.4, pp 409-461.
10. Cukier, R. I.; Nocera, D. G. Annu. Rev. Phys. Chem. 1998, 49, 337-369.
11. Stubbe, J.; Nocera, D. G.; Yee, C. S.; Chang, M. C. Y. Chem. Rev. 2003, ASAP.
12. Chang, C. J.; Chang, M. C. Y.; Damrauer, N. H.; Nocera, D. G. Biochim. Biophys. Acta, accepted for publication.
13. Chang, C. J.; Chng, L. L.; Nocera, D. G. J. Am. Chem. Soc. 2003, 125, 1866-1876.
14. Chang, C. J.; Yeh, C.-Y.; Nocera, D. G. J. Org. Chem. 2002, 67, 1403-1406.
15. Yeh, C.-Y.; Chang, C. J.; Nocera, D. G. J. Am. Chem. Soc. 2001, 123, 1513-1514.
16. Chng, L. L.; Chang, C. J.; Nocera, D. G. J. Org. Chem. 2003, 68, 4075-4078.
17. Deng, Y.; Chang, C. K.; Nocera, D. G. Angew. Chem., Int. Ed. 2000, 39, 1066-1068.
18. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
19. Lindsey, J. S.; Wagner, R. W. J. Org. Chem. 1989, 54, 828-836.
20. Ishiyama, T.; Ishida, K.; Miyaura, N. Tetrahedron 2001, 57, 9813-9816.
21. Sosnovsky, G.; Krogh, J. A.; Umhoefer, S. G. Synthesis 1979, 722-724.
22. Levin, J. I.; Turos, E.; Weinreb, S. M. Synth. Commun. 1982, 12, 989-993.
23. Yeh, C.-Y.; Miller, S. E.; Carpenter, S. D.; Nocera, D. G. Inorg. Chem. 2001, 40, 3643-3646.
24. Serjeant, E. P.; Dempsey, B. Ionization Constants of Organic Acids in Aqueous Solutions; Pergamon Press: Elmsford, NY, 1979.
25. Albert, A.; Serjeant, E. P. The Determination of Ionization Constants. A Laboratory Manual, 3rd ed.; Chapman and Hall: New York, 1984.
26. Duncan, I. A.; Harriman A.; Porter, G. Anal. Chem. 1979, 51, 2206-2208.