Organic/fluorous phase extraction: A new tool for the isolation of organometallic complexes

Organometallics

Volumn 17, Issue 8, 1998, Pages 1458-1459

  Spetseris, Nikolaos ^a   Hadida, Sabine ^a   Curran, Dennis P ^a   Meyer, Tara Y ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000411860     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980058a     Document Type: Article

References (20)

1. The selective solubility of fluorinated organometallics in organic/ fluorous biphasic mixtures has been explored and, in some cases, exploited for product separation in catalytic processes, (a) Hórvath, I. T.; Rábai, J. Science 1994, 266, 72. (b) Hughes, R. P.; Trujillo, H. A. Organometallics 1996, 15, 286. (c) DiMagno, S. G.; Dussault, P. H.; Schultz, J. A. J. Am. Chem. Soc. 1996, 118, 5312. (d) Hoshino, M.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Juliette, J. J. J.; Horváth, I. T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1610. (f) Guillevic, M.-A.; Arif, A. M.; Horváth, I. T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1612.
2. The selective solubility of fluorinated organometallics in organic/ fluorous biphasic mixtures has been explored and, in some cases, exploited for product separation in catalytic processes, (a) Hórvath, I. T.; Rábai, J. Science 1994, 266, 72. (b) Hughes, R. P.; Trujillo, H. A. Organometallics 1996, 15, 286. (c) DiMagno, S. G.; Dussault, P. H.; Schultz, J. A. J. Am. Chem. Soc. 1996, 118, 5312. (d) Hoshino, M.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Juliette, J. J. J.; Horváth, I. T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1610. (f) Guillevic, M.-A.; Arif, A. M.; Horváth, I. T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1612.
3. The selective solubility of fluorinated organometallics in organic/ fluorous biphasic mixtures has been explored and, in some cases, exploited for product separation in catalytic processes, (a) Hórvath, I. T.; Rábai, J. Science 1994, 266, 72. (b) Hughes, R. P.; Trujillo, H. A. Organometallics 1996, 15, 286. (c) DiMagno, S. G.; Dussault, P. H.; Schultz, J. A. J. Am. Chem. Soc. 1996, 118, 5312. (d) Hoshino, M.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Juliette, J. J. J.; Horváth, I. T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1610. (f) Guillevic, M.-A.; Arif, A. M.; Horváth, I. T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1612.
4. The selective solubility of fluorinated organometallics in organic/ fluorous biphasic mixtures has been explored and, in some cases, exploited for product separation in catalytic processes, (a) Hórvath, I. T.; Rábai, J. Science 1994, 266, 72. (b) Hughes, R. P.; Trujillo, H. A. Organometallics 1996, 15, 286. (c) DiMagno, S. G.; Dussault, P. H.; Schultz, J. A. J. Am. Chem. Soc. 1996, 118, 5312. (d) Hoshino, M.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Juliette, J. J. J.; Horváth, I. T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1610. (f) Guillevic, M.-A.; Arif, A. M.; Horváth, I. T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1612.
5. The selective solubility of fluorinated organometallics in organic/ fluorous biphasic mixtures has been explored and, in some cases, exploited for product separation in catalytic processes, (a) Hórvath, I. T.; Rábai, J. Science 1994, 266, 72. (b) Hughes, R. P.; Trujillo, H. A. Organometallics 1996, 15, 286. (c) DiMagno, S. G.; Dussault, P. H.; Schultz, J. A. J. Am. Chem. Soc. 1996, 118, 5312. (d) Hoshino, M.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Juliette, J. J. J.; Horváth, I. T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1610. (f) Guillevic, M.-A.; Arif, A. M.; Horváth, I. T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1612.
6. The selective solubility of fluorinated organometallics in organic/ fluorous biphasic mixtures has been explored and, in some cases, exploited for product separation in catalytic processes, (a) Hórvath, I. T.; Rábai, J. Science 1994, 266, 72. (b) Hughes, R. P.; Trujillo, H. A. Organometallics 1996, 15, 286. (c) DiMagno, S. G.; Dussault, P. H.; Schultz, J. A. J. Am. Chem. Soc. 1996, 118, 5312. (d) Hoshino, M.; Curran, D. P. J. Org. Chem. 1997, 62, 8341. (e) Juliette, J. J. J.; Horváth, I. T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1610. (f) Guillevic, M.-A.; Arif, A. M.; Horváth, I. T.; Gladysz, J. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1612.
7. Wigley, D. A.; Gray, S. D. In Comprehensive Organometallic Chemistry II; Labinger, J. A., Winter, M. J., Eds.; Pergamon: Oxford, 1995; Vol. 5, pp 57-154.
8. (a) Sanner, R. D.; Carter, S. T.; Bruton, W. J. J. Organomet. Chem. 1982, 240, 157.
9. (b) Gibson, V. C.; Bercaw, J. E.; Bruton, W. J., Jr.; Sanner, R. D. Organometallics 1986, 5, 976.
10. (c) Yasuda, H.; Okamoto, T.; Nakamura, A. In Organometallic Synthesis; King, R. B.; Eisch, J. J., Eds.; Elsevier: New York, 1988; Vol. 4, pp 22-23.
11. (d) Bunker, M. J.; de Clan, A.; Green, M. L. H.; Moreau, J. J. E.; Singanporia, N. J. Chem. Soc., Dalton Trans. 1980, 2155.
12. (a) Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. Science 1997, 275, 823.
13. (b) Curran, D. P. Angew. Chem., Int. Ed. Engl. 1997, in press.
14. (c) Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917.
15. (d) Curran, D. P. Chemtracts-Org. Chem. 1996, 9, 75.
16. Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531.
17. 13).
18. 5, 15H).
19. 19F NMR of the recrystallized product showed no evidence of incorporation of fluorine into the niobium complex.
20. de la Mata, J.; Fandos, R.; Gómez, M.; Gómez-Sal, P.; Martinez-Carrera, S.; Royo, P. Organometallics 1990, 9, 2846.