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Volumn 47, Issue 35, 2008, Pages 6638-6642

Ruthenium porphyrin-catalyzed aerobic oxidation of terminal aryl alkenes to aldehydes by a tandem epoxidation-isomerization pathway

Author keywords

Alkenes; Homogeneous catalysis; N ligands; Oxidation; Ruthenium

Indexed keywords

ALDEHYDES; CATALYSIS; CHEMICAL OXYGEN DEMAND; ELECTRON TRANSITIONS; HYDROCARBONS; ISOMERIZATION; ISOMERS; OLEFINS; ORGANIC COMPOUNDS; OXIDATION; PORPHYRINS; PORT TERMINALS; RUTHENIUM; VEGETATION;

EID: 52449104777     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801500     Document Type: Article
Times cited : (97)

References (54)
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    • 8= octachlorotetrakis(pentafluorophenyl) porphyrinato dianion) can catalyze aerobic oxidation of styrene at room temperature to primarily afford an aldehyde. However, this process results in a complete C=C bond cleavage to give benzaldehyde. See: E. R. Birnbaum, J. A. Labinger, J. E. Bercaw, H. B. Gray, Inorg. Chim. Acta 1998, 270, 433-439.
    • 8= octachlorotetrakis(pentafluorophenyl) porphyrinato dianion) can catalyze aerobic oxidation of styrene at room temperature to primarily afford an aldehyde. However, this process results in a complete C=C bond cleavage to give benzaldehyde. See: E. R. Birnbaum, J. A. Labinger, J. E. Bercaw, H. B. Gray, Inorg. Chim. Acta 1998, 270, 433-439.
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    • For other types of 2a-catalyzed aerobic oxidation, such as alkene epoxidation and amine dehydrogenation, see: a J. T. Groves, R. Quinn, J. Am. Chem. Soc. 1985, 107, 5790-5792;
    • For other types of 2a-catalyzed aerobic oxidation, such as alkene epoxidation and amine dehydrogenation, see: a) J. T. Groves, R. Quinn, J. Am. Chem. Soc. 1985, 107, 5790-5792;
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    • CCDC 683003 contains the supplementary crystallographic data for this paper, Crystallographic Data Centre at
    • CCDC 683003 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre at www.ccdc.cam. ac.uk/data_request/cif.
    • These data can be obtained free of charge from The Cambridge
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    • 4. See: Z. Gross, C. M. Barzilay, J. Chem. Soc. Chem. Commun. 1995, 1287-1288. One referee suggested that the superiority of chlorinated solvents in the catalytic oxidation reported in this work could be related to the fact that these solvents could recycle some of the ruthenium-(carbonyl)complexes back to dichlororuthenium(IV) or related species.
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    • Currently we cannot exclude the possibility that small amounts of the arylacetaldehydes 4 resulted from a direct oxidation of the corresponding aryl alkenes rather than from isomerization of epoxides. For examples of arylacetaldehyde formation from direct oxidation of styrenes by oxoiron porphyrins or by iodosylbenzene or hypochlorite in the presence of iron and manganese porphyrin catalysts, see: a J. T. Groves, R. S. Myers, J. Am. Chem. Soc. 1983, 105, 5791-5796;
    • Currently we cannot exclude the possibility that small amounts of the arylacetaldehydes 4 resulted from a direct oxidation of the corresponding aryl alkenes rather than from isomerization of epoxides. For examples of arylacetaldehyde formation from direct oxidation of styrenes by oxoiron porphyrins or by iodosylbenzene or hypochlorite in the presence of iron and manganese porphyrin catalysts, see: a) J. T. Groves, R. S. Myers, J. Am. Chem. Soc. 1983, 105, 5791-5796;
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