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

Organometallics

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

  Chevrin, Carole ^a   Le Bras, Jean ^a   Hénin, Françoise ^a   Muzart, Jacques ^a   Pla Quintana, Anna ^b   Roglans, Anna ^b   Pleixats, Roser ^c  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

^b UNIVERSITY OF GIRONA   (Spain)

^c UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

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

ALLYLIC SUBSTITUTION; DIAZONIUM SALTS; ISOTOPOMERIC IONS; NUCLEOPHILICITY;

PALLADIUM;

EID: 4944232693     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0495877     Document Type: Article

References (32)

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23. 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.
24. c
25. H, and 2.
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27. 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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29. 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.
30. 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.
31. 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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