Addition of carboxyalkyl radicals to alkenes through a catalytic process, using a Mn(II)/Co(II)/O2 redox system

Journal of Organic Chemistry

Volumn 68, Issue 15, 2003, Pages 5974-5976

  Hirase, Koji ^a   Sakaguchi, Satoshi ^a   Ishii, Yasutaka ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

REDOX SYSTEMS;

ADDITION REACTIONS; CARBOXYLIC ACIDS; CATALYST ACTIVITY; MANGANESE; REDOX REACTIONS;

OLEFINS;

ACID ANHYDRIDE; ALKADIENE; ALKENE; ALKYL GROUP; CARBOXYLIC ACID DERIVATIVE; COBALT; DICARBOXYLIC ACID DERIVATIVE; MANGANESE; OXYGEN; RADICAL;

ADDITION REACTION; ARTICLE; CATALYSIS; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; TECHNIQUE;

EID: 0038373015     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034584+     Document Type: Article

References (21)

1. (a) Renaud, P.; Sibi, M. P. Radicals in Organic Synthesis; Vol. 1, Basic principles; Vol. 2, Applications; Wiley-VCH: New York, 2001.
2. (b) Motherwell, W. B.; Chich, D. Free Radical Chain Reactions in Organic Synthesis; Academic: London, UK, 1992.
3. (c) Curran, D. P. Comprehensive Organic Synthesis; Trost, B., Fleming, M. I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 4, Chapters 4.1 and 4.2.
4. (d) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, UK, 1986.
5. (e) Migs, W. J.; de Jonge, C. R. H. I. Organic Synthesis by Oxidation with Metal Compounds; Plenam Press: New York, 1986.
6. (a) Finkbeiner, H. L.; Bush, J. B., Jr. Discuss. Faraday Soc. 1968, 46, 150.
7. (b) Bush, J. B. Jr.; Finkbeiner, H. L. J. Am. Chem. Soc. 1968, 90, 5903.
8. (a) Heiba, E. I.; Dessau, R. M.; Koehl, W. J., Jr. J. Am. Chem. Soc. 1969, 91, 138.
9. (b) Heiba, E. I.; Dessau, R. M.; Koehl, W. J., Jr. J. Am. Chem. Soc. 1968, 90, 5905.
10. Iwahama, T.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 2000, 2317.
11. Hirase, K.; Iwahama, T.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2002, 67, 970.
12. (a) Basolo, F.; Jones, R. D.; Summerville, D. A. Chem. Rev. 1979, 79, 139.
13. (b) Wong, C. L.; Switer, J. A.; Balakrishnan, K. P.; Endicott, J. F. J. Am. Chem. Soc. 1980, 102, 5511.
14. (c) Drago, R. S.; Cannady, J. P.; Leslie, K. A. J. Am. Chem. Soc. 1980, 102, 6014.
15. Linker, T.; Kersten, B.; Linker, U.; Peter, K.; Peter, E.; von Schnering, H. G. Synlett 1996, 468.
16. Jayasree, S.; Seayad, A.; Chaudhari, R. V. Org. Lett. 2000, 2, 203.
17. Monflier, E.; Tilloy, S.; Bertoux, F.; Castanet, Y.; Mortreux, A. New J. Chem. 1997, 21, 857.
18. Greve, B.; Imming, P.; Laufer, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1221.
19. Ceccherelli, P.; Curini, M.; Marcotullio, M. C.; Pisani, E.; Rosati, O.; Wenkert, E. Tetrahedron 1997, 53, 8501.
20. Azuma, H. JP 93-245413, 1993 (AN 1995: 662976).
21. Gates, M.; Malchick, S. P. J. Am. Chem. Soc. 1957, 79, 5546.