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Volumn 23, Issue 20, 2004, Pages 4796-4799

Allylic substitution mediated by water and palladium: Unusual role of a palladium(II) catalyst and ESI-MS analysis

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CATALYSIS; CATALYSTS; COMPLEXATION; MASS SPECTROMETRY; MIXTURES; NEGATIVE IONS; SODIUM COMPOUNDS; SUBSTITUTION REACTIONS; WATER;

EID: 4944232693     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0495877     Document Type: Article
Times cited : (47)

References (32)
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    • (a) For a monograph on ESI-MS: Cole, R. B. Electrospray Ionization Mass Spectrometry, Fundamentals, Instrumentation and Applications; Wiley: New York, 1997. For the application of ESI-MS to inorganic and Organometallic chemistry, see the following reviews and references therein: (b) Colton, R.; D'Agostino, A.; Traeger, J. C. Mass Spectrom. Rev. 1995, 14, 79. (c) Henderson, W.; Nicholson, B. K.; McCaffrey, L. J. Polyhedron 1998, 17, 4291. (d) Traeger, J. C. Int. J. Mass Spectrom. 2000, 200, 387. (e) Plattner, D. A. Int. J. Mass Spectrom. 2001, 207, 125.
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    • note
    • 2O) was delivered by a P2000 HPLC pump (ThermoQuest) to the vaporization nozzle of the electrospray ion source (165°C for BSI(+) and 140°C for ESI(-)), and nitrogen was employed as both a drying and a nebulizing gas. Skimmer cone voltages were varied between 10 and 100 eV. Spectra were typically an average of 15-20 scans. Theoretical isotope patterns were calculated by use of the Isoform program and used to aid assignment.
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    • note
    • c
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    • H, and 2.
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    • Several kinds of coordination modes are known between Pd(II) and acetylacetone; see: (a) Kanda, Z.; Nakamura, Y.; Kawaguehi, S. Inorg. Chem. 1978, 17,910. (b) Otani, Y.; Nakamura, Y.; Kawaguchi, S.; Okeya, S. Hinomoto, T. Bull. Chem. Soc. Jpn. 1982, 55, 1467. The O,C,O′ chelation was chosen in our case according to the reactivity of the palladium enolate complex with 1.
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    • Several kinds of coordination modes are known between Pd(II) and acetylacetone; see: (a) Kanda, Z.; Nakamura, Y.; Kawaguehi, S. Inorg. Chem. 1978, 17,910. (b) Otani, Y.; Nakamura, Y.; Kawaguchi, S.; Okeya, S. Hinomoto, T. Bull. Chem. Soc. Jpn. 1982, 55, 1467. The O,C,O′ chelation was chosen in our case according to the reactivity of the palladium enolate complex with 1.
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    • For the preparation of palladium etiolate complexes of 1,3-diketones, see: (a) Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361. (b) Nowotny, M.; Henefeld, U.; Van Koningsveld, H.; Maschmeyer, T. Chem. Commun. 2000, 1877. (c) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240 and references cited therein, (d) Gavrielatos, E.; Athanasellis, G.; Heaton, B. T.; Steiner, A.; Bickley, J. F.; Igglessi-Markopoulou, O.; Markopoulos, J. Inorg. Chim. Acta 2003, 351, 21.
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  • 29
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    • For the preparation of palladium etiolate complexes of 1,3-diketones, see: (a) Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361. (b) Nowotny, M.; Henefeld, U.; Van Koningsveld, H.; Maschmeyer, T. Chem. Commun. 2000, 1877. (c) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240 and references cited therein, (d) Gavrielatos, E.; Athanasellis, G.; Heaton, B. T.; Steiner, A.; Bickley, J. F.; Igglessi-Markopoulou, O.; Markopoulos, J. Inorg. Chim. Acta 2003, 351, 21.
    • (2000) Chem. Commun. , pp. 1877
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  • 30
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    • For the preparation of palladium etiolate complexes of 1,3-diketones, see: (a) Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361. (b) Nowotny, M.; Henefeld, U.; Van Koningsveld, H.; Maschmeyer, T. Chem. Commun. 2000, 1877. (c) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240 and references cited therein, (d) Gavrielatos, E.; Athanasellis, G.; Heaton, B. T.; Steiner, A.; Bickley, J. F.; Igglessi-Markopoulou, O.; Markopoulos, J. Inorg. Chim. Acta 2003, 351, 21.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 11240
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  • 31
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    • For the preparation of palladium etiolate complexes of 1,3-diketones, see: (a) Shaw, B. L.; Perera, S. D.; Staley, E. A. Chem. Commun. 1998, 1361. (b) Nowotny, M.; Henefeld, U.; Van Koningsveld, H.; Maschmeyer, T. Chem. Commun. 2000, 1877. (c) Hamashima, Y.; Hotta, D.; Sodeoka, M. J. Am. Chem. Soc. 2002, 124, 11240 and references cited therein, (d) Gavrielatos, E.; Athanasellis, G.; Heaton, B. T.; Steiner, A.; Bickley, J. F.; Igglessi-Markopoulou, O.; Markopoulos, J. Inorg. Chim. Acta 2003, 351, 21.
    • (2003) Inorg. Chim. Acta , vol.351 , pp. 21
    • Gavrielatos, E.1    Athanasellis, G.2    Heaton, B.T.3    Steiner, A.4    Bickley, J.F.5    Igglessi-Markopoulou, O.6    Markopoulos, J.7


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