Facile synthesis of (η5-Ph4C4COH)(CO)2RuCl and catalytic oxidation of alcohols with chloroform

Organometallics

Volumn 21, Issue 25, 2002, Pages 5674-5677

  Jung, Hyun Min ^a   Choi, Jun Ho ^a   Lee, Soon Ok ^a   Kim, Yu Hwan ^a   Park, Jung Hye ^a   Park, Jaiwook ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC OXIDATION;

ALCOHOLS; CATALYSIS; CATALYSTS; ETHANOL; HYDROGEN; OXIDATION; RUTHENIUM COMPOUNDS; SODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

ORGANOMETALLICS;

EID: 0038339007     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020516m     Document Type: Article

References (22)

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2. Menashe, N.; Shvo, Y. Organometallics 1991, 10, 3885.
3. Shvo, Y.; Czarkie, D. J. Organomet. Chem. 1986, 315, C25.
4. (a) Almeida, M. L. S.; Beller, M.; Wang, G.-Z.; Bäckvall, J.-E. Chem. Eur. J. 1996, 2, 1533.
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10. (c) Kim, M.-J.; Choi, Y. K.; Choi, M. Y.; Kim, M. J.; Park, J. J. Org. Chem. 2001, 66, 4736.
11. 12 in chloroform: Choi, J. H.; Kim, Y. H.; Nam, S. H.; Shin, S. T.; Kim, M.-J.; Park, J. Angew. Chem., Int. Ed. 2002, 41, 2373.
12. 13C NMR data for 2 are different from those reported previously: Bailey, N. A.; Jassai, V. S.; Vefghi, R.; White, C. J. Chem. Soc., Dalton Trans. 1987, 2815.
13. 2: Casey, C. P.; Vos, T. E.; Singer, S. W.; Guzei, I. A. Organometallics 2002, 21, 5038.
14. 4 coordination: Blum, Y.; Shvo, Y.; Chodosh, D. F. Inorg. Chim. Acta 1985, 97, L25.
15. The iodide analogue of 2 is reported to be formed in the reaction of the Shvo complex with iodomethane or iodine: Schneider, B.; Goldberg, I.; Reshef, D.; Stein, Z.; Shvo, Y. J. Organomet. Chem. 1999, 588, 92. The iodide analogue also acts as an oxidation catalyst under the conditions of the entry 4 in Table 1, but its reactivity is much lower than that of 2 (44% yield after 48 h).
16. Csjernyik, G.; Éll, A. H.; Fadini, L.; Pugin, B.; Bäckvall, J.-E. J. Org. Chem. 2002, 67, 1657 and references therein.
17. 1H NMR spectrum. The characteristic peak for the hydride of 1 was observed at - 18.3 ppm.
18. The suggestion of dichlorocarbene complex 6 as an intermediate is supported by the previous examples that show generation of metal dichlorocarbene complexes from the activation of chloroform as isolable compounds as well as reactive intermediates: (a) Park, J. H.; Koh, J. H.; Park, J. Organometallics 2001, 20, 1892.
19. (b) Grushin, V. V.; Alper, H. Organometallics 1993, 12, 3846 and references therein.
20. In a separate experiment, a radical scavenger 2,4,6-trimethylphenol did not inhibit the catalytic oxidation of 1-phenylethanol.
21. (a) Mays, M. J.; Morris, M. J.; Raithby, P. R.; Shvo, Y.; Czarkie, D. Organometallics 1989, 8, 1162.
22. (b) Casey, C. P.; Singer, S. W.; Powell, D. R.; Hayashi, R. K.; Kavana, M. J. Am. Chem. Soc. 2001, 123, 1090.