Synthesis and reactivity of a mono-σ-aryl palladium(IV) fluoride complex

Journal of the American Chemical Society

Volumn 131, Issue 11, 2009, Pages 3796-3797

  Ball, Nicholas D ^a   Sanford, Melanie S ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL FLUORIDES; BIPYRIDINE; BOND FORMATION; CATALYZED COUPLING; FLUORIDE COMPLEXES; RATIONAL DESIGN;

COMPLEXATION; FLUORINE COMPOUNDS; PALLADIUM;

PALLADIUM COMPOUNDS;

CARBON; FLUORIDE; LIGAND; PALLADIUM COMPLEX; 2,2' BIPYRIDINE; FLUORINATED HYDROCARBON; ORGANOMETALLIC COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; FLUORINATION; FLUORINE NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STOICHIOMETRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY; CHEMISTRY;

2,2'-DIPYRIDYL; CATALYSIS; FLUORIDES; HYDROCARBONS, FLUORINATED; ORGANOMETALLIC COMPOUNDS; PALLADIUM;

EID: 67749111679     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8054595     Document Type: Article

References (34)

1. Thayer, A. M. Chem. Eng. News 2006, 23, 15.
2. (a) Kirk, K. L. Org. Process Res. Dev. 2008,12, 305, and references therein.
3. (b) Banks, R. E.; Tatlow, J. C., Smart, B. E. Organofluorine Chemistry: Principles and Commercial Applications; Plenum Press: New York, 1994; pp 25-55.
4. (c) Gouverneur, V.; Greedy, B. Chem.-Eur. J. 2002, 5, 767.
5. (d) Sun, H.; DiMagno, S. G. J. Am. Chem. Soc. 2005, 127, 2050.
6. For examples, see:(a) Balz, G.; Schiemann, G. Ber. Dtsch. Chem. Ges. 1927, 60, 1186.
7. (b) Sun, H.; DiMagno, S. G. Angew. Chem., Int. Ed. 2006, 45, 2720.
8. Grushin, V. V. Chem.-Eur. J. 2002, 5, 1006, and references therein.
9. Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 1232.
10. (b) Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 13944.
11. Vigalok, A. Chem-Eur. J. 2008, 14, 5102.
12. a) Grushin, V. V.; Marshall, W. J. Organometallics 2007, 26, 4997.
13. (b) Yandulov, D. V.; Tran, N. T. J. Am. Chem. Soc. 2007, 129, 1342.
14. Hull, K. L.; Anani, W. Q.; Sanford, M. S. J. Am. Chem. Soc. 2006, 125, 7134.
15. (a) Kaspl, A. W.; Yahav-Levi, A.; Goldberg, I.; Vigalok, A. Inorg. Chem. 2008, 47, 5.
16. (b) Furuya, T.; Kaiser, H. M.; Ritter, T. Angew. Chem., Int. Ed. 2008, 47, 5993.
17. IV(Ar)(F) complex that undergoes C-F reductive elimination was reported while this manuscript was in preparation. See:Furuya, T.; Ritter, T. JIV. Am. Chem. Soc. 2008, 130, 10060.
18. For an organometallic Pd1V fluoride that does not undergo C-F bond- forming reductive elimination, see:Canty, A. J.; Traill, P. R.; Skelton, B. W.; White, A. H. 1JV. Organomet. Chem. 1992, 433, 213.
19. For related Pd1V complexes that undergo C- O Ac and C- Cl bond-forming reductive elimination, see:(a) Dick, A. R.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 12790.
20. (b) Whitfield, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 15142.
21. Canty, A. J. Acc. Chem. Res. 1992, 25, 83.
22. Rao, P. R.; Tressaud, A.; Bartlett, N. Inorg. Nucl. Chem. 1976, 23.
23. (a) Pilon, M. C.; Grushin, V. V. Organometallics 1998, 17, 1774.
24. (b) Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2009, 131, 918.
25. The stoichiometric fluorination described in ref 9b shows a similar tolerance of electronically diverse σ-aryl groups and comparable/slightly higher yields.
26. 2O led to an erosion of the yield of 3a (to 3%) and a significant increase in the formation of 4a (75%).
27. Selected examples ofmetal-FHFcomplexes:(a) Jasim, N. A.; Perutz, R. N. J. Am. Chem. Soc. 2000, 122, 8685.
28. (b) Roe, D. C.; Marshall, W. J.; Davidson, F.; Soper, P. D.; Grushin, V. V. Organometallics 2000, 19, 4575.
29. Appelman, E. H.; Malm, J. G. J. Am. Chem. Soc. 1964, 56, 2297.
30. Lagunas, M.-C.; Gossage, R. A.; Spek, A. L.; van Koten, G. Organome-tallics 2003, 22, 722.
31. The poor mass balance may be due to the formation of one or more inorganic byproducts, and efforts are underway to separate/characterize these species.
32. 11, see:(a) Grushin, V. V.; Marshall, W. J. J. Am. Chem. Soc. 2006, 125, 4632.
33. (b) Cardenas, D. J.; Martin- Matute, B.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 125, 5033.
34. 1V. Studies to gain further mechanistic insights into this oxidant-promoted C-F coupling process are ongoing.