Synthesis, Structure, and Oxidative Additions of a Fluorous Analogue of Vaska's Complex, trans-[IrCl(CO){P[CH2CH2(CF2) 5CF3]3}2] - Altered Reactivity in Fluorocarbons and Implications for Catalysis

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 15, 1997, Pages 1612-1615

  Guillevic, Marie Andrée ^a   Arif, Atta M ^a   Horváth, István T ^b   Gladysz, J A ^a  

^a UNIVERSITY OF UTAH   (United States)

^b EXXONMOBIL UPSTREAM RESEARCH COMPANY   (United States)

Author keywords

Iridium; Ligand effects; O O activation; Radical reactions; Two phase catalysis

Indexed keywords

EID: 0030819609     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199716121     Document Type: Article

References (28)

1. B. Corneils, W. A. Herrmann, Applied Homogeneous Catalysis with Organometallic Compounds, VCH, Weinheim, 1996.
2. a) I. T. Horváth, J. Rábai, Science 1994, 266, 72;
3. b) US-A Patent 5,463,082, 1995.
4. J. J. J. Juliette, I. T. Horváth, J. A. Gladysz, Angew. Chem. 1997, 109, 1682-1684; Angew. Chem. Int. Ed. Engl. 1997, 36, 1610-1612.
5. J. J. J. Juliette, I. T. Horváth, J. A. Gladysz, Angew. Chem. 1997, 109, 1682-1684; Angew. Chem. Int. Ed. Engl. 1997, 36, 1610-1612.
6. a) R. P. Hughes, H. A. Trujillo, Organometallics 1996, 15, 286;
7. b) S. G. DiMagno, P. H. Dussault, J. A. Schultz, J. Am. Chem. Soc. 1996, 118, 5312;
8. c) A. Studer, S. Hadida, R. Ferritto, S.-Y. Kim, P. Jeger, P. Wipf, D. P. Curran, Science 1997, 275, 823, and references therein.
9. a) L. Vaska, Science 1963, 140, 809;
10. b) P. B. Chock, J. Halpern, J. Am. Chem. Soc. 1966, 88, 3511.
11. Prior use of related reactions: M. J. Burk, R. H. Crabtree, Inorg. Chem. 1986, 25, 931.
12. 19F couplings;
13. int = 0.0324, R indices (all data): R1 = 0.0637, wR2 = 0.1442. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100 131. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB21EZ, UK. (fax: int. code +(1223)336-033; e-mail: deposit@chemcrys.cam.ac.uk).
14. 2] exhibits Ir-P, Ir-Cl, and Ir-C bond lengths of 2.347(2), 2.421(5), and 1.80(2) Å, and L-Ir-L bond angles of (90 ± 1)° and (180 ± 1)° at room temperature: L. Dahlenburg, A. Yardimcioglu, J. Organomet. Chem. 1985, 291, 371.
15. 3}]: C. R. Jablonski, Z. Zhou, Can. J. Chem. 1992, 70, 2544.
16. 3}]: C. R. Jablonski, Z. Zhou, Can. J. Chem. 1992, 70, 2544.
17. B. Albinsson, J. Michl, J. Phys. Chem. 1996, 100, 3418.
18. Reviews of several distinct mechanisms by which alkyl halides can undergo oxidative addition: a) J. P. Collman, L. S. Hegedus, J. R. Norton, R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, California, 1987, pp. 306-322; b) S. Henderson, R. A. Henderson, Adv. Phys. Org. Chem. 1987, 23, 1.
19. Reviews of several distinct mechanisms by which alkyl halides can undergo oxidative addition: a) J. P. Collman, L. S. Hegedus, J. R. Norton, R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, California, 1987, pp. 306-322; b) S. Henderson, R. A. Henderson, Adv. Phys. Org. Chem. 1987, 23, 1.
20. 2I: P. Bernatis (University of Utah), unpublished results.
21. 11 than THF.
22. J. A. Labinger, J. A. Osborn, N. J. Coville, Inorg. Chem. 1980, 19, 3236.
23. 2 to 1: P. P. Deutsch, R. Eisenberg, Chem. Rev. 1988, 88, 1147.
24. 2 to 1: M. Selke, W. L. Karney, S. I. Khan, C. S. Foote, Inorg. Chem. 1995, 34, 5715.
25. 2: L. Vaska, L. S. Chen, J. Chem. Soc. Chem. Commun. 1971, 1080.
26. P. M. Maitlis, A. Haynes, G. J. Sunley, M. J. Howard, J. Chem. Soc. Dalton Trans. 1996, 2187.
27. a) J. L. Kiplinger, T. G. Richmond, C. E. Osterberg, Chem. Rev. 1994, 94, 373;
28. b) M. J. Atherton, J. Fawcett, J. H. Holloway, E. G. Hope, A. Karaçar, D. R. Russell, G. C. Saunders, J. Chem. Soc. Dalton Trans. 1996, 3215.