Trifluoromethyl coordination and C-F bond activation at calcium

Angewandte Chemie - International Edition

Volumn 46, Issue 33, 2007, Pages 6339-6342

  Barrett, Anthony G M ^a   Crimmin, Mark R ^a   Hill, Michael S ^a   Hitchcock, Peter B ^b   Procopiou, Panayiotis A ^c  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF SUSSEX   (United Kingdom)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Alkaline earth metals; C F activation; Calcium; Fluorine; N ligands

Indexed keywords

CHEMICAL BONDS; FLUORINE; LIGANDS;

BOND CLEAVAGE; FLUORAL ARRANGEMENT; TRIFLUOROMETHYL COORDINATION;

CALCIUM COMPOUNDS;

CALCIUM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THERMODYNAMICS;

CALCIUM; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; THERMODYNAMICS;

EID: 34548273957     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200701945     Document Type: Article

References (41)

1. J. E. Huheey, E. A. Keiter, R. L. Keiter, Inorganic Chemistry, 4th ed., Harper & Collins, 1995.
2. a) J. L. Kiplinger, T. G. Richmond, C. E. Osterberg, Chem. Rev. 1994, 94, 373;
3. b) T. G. Richmond, Angew. Chem. 2000, 112, 3378;
4. Angew. Chem. Int. Ed. 2000, 39, 3241;
5. c) U. Mazurek, H. Schwarz, Chem. Commun. 2003, 1321.
6. a) L. Maron, L. Perrin, O. Eisenstein, Dalton Trans. 2003, 4313;
7. b) L. Maron, E. L. Werkema, L. Perrin, O. Eisenstein, R. A. Andersen, J. Am. Chem. Soc. 2005, 127, 279.
8. a) P. L. Watson, J. Chem. Soc. Chem. Commun. 1983, 276;
9. b) P. L. Watson, J. Am. Chem. Soc. 1983, 105, 6941;
10. c) T. D. Tilley, Acc. Chem. Res. 1993, 26, 22, and references therein;
11. d) C. M. Fendrick, T. J. Marks, J. Am. Chem. Soc. 1984, 106, 2214;
12. e) S. J. Simpson, H. W. Turner, R. A. Andersen, J. Am. Chem. Soc. 1979, 101, 7728;
13. f) A. D. Sadow, T. D. Tilley, J. Am. Chem. Soc. 2003, 125, 7971;
14. g) A. D. Sadow, T. D. Tilley, J. Am. Chem. Soc. 2005, 127, 643.
15. a) M. R. Crimmin, I. J. Casely, M. S. Hill, J. Am. Chem. Soc. 2005, 127, 2042;
16. b) M. R. Crimmin, A. G. M. Barrett, M. S. Hill, P. B. Hitchcock, P. A. Procopiou, Organometallics 2007, 26, 2953;
17. c) M. R. Crimmin, A. G. M. Barrett, M. S. Hill, P. A. Procopiou, Org. Lett. 2007, 9, 331;
18. d) F. Buch, J. Brettar, S. Harder, Angew. Chem. 2006, 118, 2807;
19. Angew. Chem. Int. Ed. 2006, 45, 2741.
20. a) M. H. Chisholm, J. C. Gallucci, K. Phomphari, Inorg. Chem. 2004, 43, 6717;
21. b) M. H. Chisholm, J. C. Gallucci, K. Phomphari, Chem. Commun. 2003, 48.
22. a) A. G. Avent, M. R. Crimmin, M. S. Hill, P. B. Hitchcock, Dalton Trans. 2004, 3166;
23. b) A. G. Avent, M. R. Crimmin, M. S. Hill, P. B. Hitchcock, Dalton Trans. 2005, 278;
24. c) A. G. Avent, M. R. Crimmin, M. S. Hill, P. B. Hitchcock, Organometallics 2005, 24, 1184;
25. d) A. G. Avent, M. R. Crimmin, M. S. Hill, P. B. Hitchcock, J. Organomet. Chem. 2006, 691, 1242;
26. e) A. G. M. Barrett, M. R. Crimmin, M. S. Hill, P. B. Hitchcock, P. A. Procopiou, Organometallics 2007, DOI: 10.1021/om070083t;
27. f) S. Harder, J. Brettar, Angew. Chem. 2006, 118, 3554;
28. Angew. Chem. Int. Ed. 2006, 45, 3474;
29. g) C. Ruspic, S. Nembenna, A. Hofmeister, J. Magull, S. Harder, H. W. Roesky, J. Am. Chem. Soc. 2006, 128, 15 000;
30. h) S. Nembenna, H. W. Roesky, S. Nagendran, A. Hofmeister, J. Magull, P. J. Wilbrandt, M. Hahn, Angew. Chem. 2007, 119, 2519;
31. Angew. Chem. Int. Ed. 2007, 46, 2512.
32. S. Harder, Angew. Chem. 2003, 115, 3553;
33. Angew. Chem. Int. Ed. 2003, 42, 3430.
34. D. T. Carey, E. K. Cope-Eatough, E. Vilaplana-Mafé, F. S. Mair, R. G. Pritchard, J. E. Warren, R. J. Woods, Dalton Trans. 2003, 1083.
35. a) H. Plenio, Chem. Rev. 1997, 97, 3363;
36. b) H. J. Buschmann, J. Hermann, M. Kaupp, H. Plenio, Chem. Eur. J. 1999, 5, 2566;
37. c) H. Plenio, ChemBioChem 2004, 5, 650, and references therein.
38. D. C. Bradley, M. Hasan, M. B. Hursthouse, M. Motevalli, O. F. Z. Khan, R. G. Pritchard, J. O. Williams, J. Chem. Soc. Chem. Commun. 1992, 575.
39. Gaussian03, Revision C.02, M.J. Frisch et al., Gaussian, Inc., Wallingford CT, 2004. All optimized structures were verified by independent frequency calculations.
40. 3)NHAr] (Ar = 2,6-diisopropylphenyl) reported to date display the N,N-chelation bonding mode; a) D. S. Laitar, C. J. N. Mathison, W. M. Davis, J. P. Sadighi, Inorg. Chem. 2003, 42, 7354;
41. b) M. S. Hill, P. B. Hitchcock, R. Pongtavornpinyo, Dalton Trans. 2005, 27.