Catalytic C-F bond activation of nonactivated monofluoroarenes

Organometallics

Volumn 18, Issue 3, 1999, Pages 294-296

  Young Jr , Robert J ^a   Grushin, Vladimir V ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003307688     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980887w     Document Type: Article

References (31)

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2. Cox, J. D.; Pilcher, G. Thermochemistry of Organic and Organometallic Compounds; Academic Press: London, 1970. McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493. Smart, B. E. In The Chemistry of Functional Groups, Suppl. D; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1983; Chapter 14.
3. Cox, J. D.; Pilcher, G. Thermochemistry of Organic and Organometallic Compounds; Academic Press: London, 1970. McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493. Smart, B. E. In The Chemistry of Functional Groups, Suppl. D; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1983; Chapter 14.
4. For reviews, see: (a) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 94, 373. (b) Burdeniuc, J.; Jedlicka, B.; Crabtree, R. H. Chem. Ber./Recl. 1997, 130, 145. (c) Richmond, T. G. Topics Organomet. Chem., in press, (d) Also, see: Murphy, E.; Murugavel, R.; Roesky, H. W. Chem. Rev. 1997, 97, 3425.
5. For reviews, see: (a) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 94, 373. (b) Burdeniuc, J.; Jedlicka, B.; Crabtree, R. H. Chem. Ber./Recl. 1997, 130, 145. (c) Richmond, T. G. Topics Organomet. Chem., in press, (d) Also, see: Murphy, E.; Murugavel, R.; Roesky, H. W. Chem. Rev. 1997, 97, 3425.
6. For reviews, see: (a) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 94, 373. (b) Burdeniuc, J.; Jedlicka, B.; Crabtree, R. H. Chem. Ber./Recl. 1997, 130, 145. (c) Richmond, T. G. Topics Organomet. Chem., in press, (d) Also, see: Murphy, E.; Murugavel, R.; Roesky, H. W. Chem. Rev. 1997, 97, 3425.
7. For reviews, see: (a) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 94, 373. (b) Burdeniuc, J.; Jedlicka, B.; Crabtree, R. H. Chem. Ber./Recl. 1997, 130, 145. (c) Richmond, T. G. Topics Organomet. Chem., in press, (d) Also, see: Murphy, E.; Murugavel, R.; Roesky, H. W. Chem. Rev. 1997, 97, 3425.
8. For most recent work in the area, see: Burdeniuc, J.; Crabtree, R. H. Organometallics 1998, 17, 1582, and references therein.
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10. 4a is unique, being equally reactive toward Ar-X bonds regardless of the nature of halogen X. In all other instances the reactivity of Ar-X toward electron-rich metal complexes decreases in the order I > Br > Cl ≫ F.
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12. Aizenberg, M.; Milstein, D. Science 1994, 94, 359; J. Am. Chem. Soc. 1995, 117, 8674. For mechanistic studies of this catalytic system, see: Edelbach, B.; Jones, W. D. J. Am. Chem. Soc. 1997, 119, 7734.
13. Aizenberg, M.; Milstein, D. Science 1994, 94, 359; J. Am. Chem. Soc. 1995, 117, 8674. For mechanistic studies of this catalytic system, see: Edelbach, B.; Jones, W. D. J. Am. Chem. Soc. 1997, 119, 7734.
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16. 2 for 48 h, other things being equal, gave 90% conversion of 1-fluoronaphthalene. However, the higher pressure and prolonged reaction time resulted in substantial hydrogenation of the aromatic ring. According to the GC-MS data naphthalene (44%), tetrahydronaphthalene (38%), 5-fluoro-1,2,3,4-tetrahydronaphthalene (7%), and decahydronaphthalene (trace) were formed in this case.
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21. 8 Similar results were obtained when the reaction was repeated in the absence of mercury metal. As the hydrogenolysis occurred, the aqueous phase stayed colorless and the organic layer was red, with no sign of Rh metal formation being observed.
22. 2O) promoters.
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24. 4F).
25. There have been precedents for activation with oxygen in the metal-catalyzed hydrogenation chemistry. See, for example: Sommovigo, M.; Alper, H. Tetrahedron Lett. 1993, 34, 59.
26. Heterogeneous systems for the hydrodefluorination of ArF with active metal hydrides have been reported. See: Caubère, P. Angew. Chem., Int. Ed. Engl. 1983, 22, 599. Carfagna, C.; Musco, A.; Pontellini, R.; Terzoni, G. J. Mol. Catal. 1989, 57, 23. Li, H.; Liao, S.; Xu, Y. Chem. Lett. 1996, 1059. Zhang, Y.; Liao, S.; Yu, D.; Shen, Q. Synth. Commun. 1997, 27, 4327.
27. Heterogeneous systems for the hydrodefluorination of ArF with active metal hydrides have been reported. See: Caubère, P. Angew. Chem., Int. Ed. Engl. 1983, 22, 599. Carfagna, C.; Musco, A.; Pontellini, R.; Terzoni, G. J. Mol. Catal. 1989, 57, 23. Li, H.; Liao, S.; Xu, Y. Chem. Lett. 1996, 1059. Zhang, Y.; Liao, S.; Yu, D.; Shen, Q. Synth. Commun. 1997, 27, 4327.
28. Heterogeneous systems for the hydrodefluorination of ArF with active metal hydrides have been reported. See: Caubère, P. Angew. Chem., Int. Ed. Engl. 1983, 22, 599. Carfagna, C.; Musco, A.; Pontellini, R.; Terzoni, G. J. Mol. Catal. 1989, 57, 23. Li, H.; Liao, S.; Xu, Y. Chem. Lett. 1996, 1059. Zhang, Y.; Liao, S.; Yu, D.; Shen, Q. Synth. Commun. 1997, 27, 4327.
29. Heterogeneous systems for the hydrodefluorination of ArF with active metal hydrides have been reported. See: Caubère, P. Angew. Chem., Int. Ed. Engl. 1983, 22, 599. Carfagna, C.; Musco, A.; Pontellini, R.; Terzoni, G. J. Mol. Catal. 1989, 57, 23. Li, H.; Liao, S.; Xu, Y. Chem. Lett. 1996, 1059. Zhang, Y.; Liao, S.; Yu, D.; Shen, Q. Synth. Commun. 1997, 27, 4327.
30. Grushin, V. V. Acc. Chem. Res. 1993, 26, 279.
31. Grushin, V. V. Unpublished observations (1988-1989).