Xenon difluoride induced aryl iodide reductive elimination: A simple access to difluoropalladium(II) complexes

Inorganic Chemistry

Volumn 47, Issue 1, 2008, Pages 5-7

  Kaspi, Ariela W ^a   Yahav Levi, Anette ^a   Goldberg, Israel ^a   Vigalok, Arkadi ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORIDE; IODINATED HYDROCARBON; ORGANOMETALLIC COMPOUND; PALLADIUM; UNCLASSIFIED DRUG; XENON; XENON FLUORIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; FLUORIDES; HYDROCARBONS, IODINATED; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM; XENON;

EID: 38749098194     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic701722f     Document Type: Article

References (27)

1. (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Sausalito, CA, 1987.
2. (b) Tsuji, J. Palladium in Organic Synthesis (Topics in Organometallic Chemistry); Springer: Berlin, 2005.
3. (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
4. (b) Bedford, R. B.; Cazin, C. S. J.; Holder, D. Coord. Chem. Rev. 2004, 248, 2283.
5. Dekleva, T. W.; Forster, D. Adv. Catal. 1986, 34, 81.
6. (a) Ettorre, R. Inorg. Nucl. Chem. Lett. 1969, 5, 45.
7. (b) In our hands, the reaction appeared to be more complex, giving large amounts of a byproduct.
8. (a) Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 13944.
9. (b) Roy, A. H.; Hartwig, J. F. Organometallics 2004, 23, 1533.
10. Yahav-Levi, A.; Goldberg, I.; Vigalok, A. J. Am. Chem. Soc. 2006, 128, 8710.
11. Yahav, A.; Goldberg, I.; Vigalok, A. J. Am. Chem. Soc. 2003, 125, 13634.
12. Fluoride migration to the coordinated phosphine ligand is the most common decomposition pathway for late-transition-metal fluoro complexes: (a) Grushin, V. V. Organometallics 2000, 19, 1888.
13. (b) Marshall, W. J.; Grushin, V. V. Organometallics 2003, 22, 555.
14. 5 group are known: (a) Albeniz, A. C.; Espinet, P.; Martin-Ruiz, B.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 11504.
15. (b) Korenaga, T.; Kosaki, T.; Fukumura, R.; Ema, T.; Sakai, T. Org. Lett. 2005, 7, 4915.
16. (c) Frohn, H.-J.; Adonin, N. Y.; Bardin, V. V.; Starichenko, V. F. Tetrahedron Lett. 2002, 43, 8111.
17. 2 data (SHELXL-97; 361 parameters with no restraints). R1 = 0.0356, wR2 = 0.0466 for 11 587 data with I > 2σ(I) and R1 = 0.0902, wR2 = 0.0978 for all unique data.
18. Grushin, V. V.; Marshall, W. J. Angew. Chem., Int. Ed. 2002, 41, 4476.
19. (a) Yahav, A.; Goldberg, I.; Vigalok, A. Inorg. Chem. 2005, 44, 1547.
20. (b) Yahav, A.; Goldberg, I.; Vigalok, A. Organometallics 2005, 24, 5654.
21. Cockman, R. W.; Ebsworth, E. A. V.; Holloway, J. H.; Murdoch, H.; Robertson, N.; Watson, P. G. In Fluorine Chemistry (Toward the 21st Century); Thrasher, J. S., Strauss, S. H., Eds.; American Chemical Society: Washington, DC, 1994; Chapter 20, p 327.
22. IV compound was recently characterized at low temperature: Canty, A. J.; Rodemann, T.; Skelton, B. W.; White, A. H. Organometallics 2006, 25, 3996.
23. 6
24. II center for the aryl ligand bearing a strong electron-accepting nitro group [(a) Yandulov, D. V.; Tran, N. T. J. Am. Chem. Soc. 2007, 129, 1342]
25. has been contested: (b) Grushin, V. V.; Marshall, W. J. Organometallics 2007, 26, 4997.
26. For the ligand-assisted synthesis of fluoroarenes using the electrophilic N-F reagents, see: Hull, K. L.; Anani, W. Q.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 7134.
27. Seppelt, K. Z. Anorg. Allg. Chem. 2003, 629, 2427.