Copper(I) Complexes of a Heavily Fluorinated β-Diketiminate Ligand: Synthesis, Electronic Properties, and Intramolecular Aerobic Hydroxylation

Inorganic Chemistry

Volumn 42, Issue 23, 2003, Pages 7354-7356

  Laitar, David S ^a   Mathison, Casey J N ^a   Davis, William M ^a   Sadighi, Joseph P ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL DERIVATIVE; COPPER BETA DIKETIMINATE; COPPER COMPLEX; FLUORINE DERIVATIVE; LIGAND; UNCLASSIFIED DRUG;

AEROBIC METABOLISM; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; COMPLEX FORMATION; HYDROXYLATION; INFRARED SPECTROSCOPY; LIGAND BINDING; SYNTHESIS; WITTIG REACTION; X RAY CRYSTALLOGRAPHY;

EID: 0242441454     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic035056j     Document Type: Article

References (39)

1. See for example: (a) Muldoon, J.; Brown, S. N. Org. Lett. 2002, 4, 1043-1045.
2. (b) Nishiyama, Y.; Nakagawa, Y.; Mizuno, N. Angew. Chem., Int. Ed. 2001, 40, 3639-3641.
3. (c) Döbler, C.; Mehltretter, G.; Beller, M. Angew. Chem., Int. Ed. 1999, 38, 3026-3028.
4. (d) Stahl, S. S.; Labinger, J. A.; Bercaw, J. E. Angew. Chem., Int. Ed. 1998, 37, 2180-2192.
5. (a) Kitajima, N.; Moro-oka, Y. Chem. Rev. 1994, 94, 737-757.
6. (b) Karlin, K. D.; Kaderli, S.; Zuberbühler, A. D Acc. Chem. Res. 1997, 30, 139-147.
7. (c) Halfen, J. A.; Mahapatra, S.; Wilkinson, E. C.; Kaderli, S.; Young, V. G., Jr.; Que, L., Jr.; Zuberbühler, A. D.; Tolman, W. B. Science 1996, 271, 1397-1400.
8. (d) Straub, B. F.; Rominger, F.; Hofmann, P. Chem. Commun. 2000, 1611-1612.
9. (e) Taki, M.; Itoh, S.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 6203-6204.
10. Selected references: (a) Pidcock, E.; Obias, H. V.; Zhang, C. X.; Karlin, K. D.; Solomon, E. I. J. Am. Chem. Soc. 1998, 120, 7841-7847.
11. (b) Holland, P. L.; Rodgers, K. R.; Tolman, W. B. Angew. Chem., Int. Ed. 1999, 38, 1139-1142.
12. (c) Itoh, S.; Taki, M.; Nakao, H.; Holland, P. L.; Tolman, W. B.; Que, L., Jr. Angew. Chem., Int. Ed. 2000, 39, 398-400.
13. (d) Taki, M.; Teramae, S.; Nagatomo, S.; Tachi, Y.; Kitagawa, T.; Itoh, S.; Fukuzumi, S. J. Am. Chem. Soc. 2002, 124, 6367-6377.
14. (e) Mirica, L. M.; Vance, M.; Jackson Rudd, D.; Hedman, B.; Hodgson, K. O.; Solomon, E. I.; Stack, T. D. P. J. Am. Chem. Soc. 2002, 124, 9332-9333.
15. (f) Zhang, C. X.; Liang, H.-C.; Kim, E-i.; Shearer, J.; Helton, M. E.; Kim, E.; Kaderli, S.; Incarvito, C. D.; Zuberbühler, A. D.; Rheingold, A. L.; Karlin, K. D. J. Am. Chem. Soc. 2003, 125, 634-635.
16. (a) Dai, X.; Warren, T. H. Chem. Commun. 2001, 1998-1999.
17. (b) Spencer, D. J. E.; Aboelella, N. W.; Reynolds, A. M.; Holland, P. L. ; Tolman, W. B. J. Am. Chem. Soc. 2002, 124, 2108-2109.
18. (c) Spencer, D. J. E.; Reynolds, A. M.; Holland, P. L.; Jazdzewski, B. A.; Duboc-Toia, C.; Le Pape, L.; Yokota, S.; Tachi, Y.; Itoh, S.; Tolman, W. B. Inorg. Chem. 2002, 41, 6307-6321.
19. (d) Aboelella, N. W.; Lewis, E. A.; Reynolds, A. M.; Brennessel, W. W.; Cramer, C. J.; Tolman, W. B. J. Am. Chem. Soc. 2002, 124, 10660-10661.
20. β-Diketimines formally derived from 1,1,1-trifluoro-2, 4-pentanedione have been synthesized: (a) Fustero, S.; de la Torre, M. G.; Pina, B.; Fuentes, A. S. J. Org. Chem. 1999, 64, 5551-5556.
21. Such ligands have been used to advantage in catalysis: (b) Allen, S. D.; Moore, D. R.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2002, 124, 14284-14285.
22. (a) The synthesis of N,N′-bis(2-mercaptophenyl) β-diketimines by condensation of the aniline with 1,1,1,5,5,5-hexafluoro-2,4-pentanedione has been reported, but no specific details are given: Sharma, R. K.; Singh, Y.; Rai, A. K. Main Group Met. Chem. 2000, 23, 777-780.
23. (b) While this work was in progress, the N,N′ -bis(2,6-diisopro-pylphenyl) analogue of 1, and its lithium salt, were reported: Carey, D. T.; Cope-Eatough, E. K.; Vilaplana-Mafé, E.; Mair, F. S.; Pritchard, R. G.; Warren, J. E.; Woods, R. J. Dalton Trans. 2003, 1083-1093.
24. (a) For a review, see: Molina, P.; Vilaplana, M. J. Synthesis 1994, 1197-1218.
25. (b) Preparation of α-diimines by this reaction: Zhong, H. A.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 2002, 124, 1378-1399.
26. The synthesis and autoxidation of 2b have been presented in oral form: Sadighi, J. P.; Laitar, D. S. Abstracts of Papers, 224th National Meeting of the American Chemical Society, Boston, MA, Aug. 18-22, 2002; American Chemical Society: Washington, DC, 2003; INOR-318.
27. Feldman, J.; McLain, S. J.; Parthasarathy, A.; Marshall, W. J.; Calabrese, J. C.; Arthur, S. D. Organometallics 1997, 16, 1514-1516.
28. int = 0,0415). No absorption correction was applied. The least squares refinement converged normally with residuals of R1 (based on F) = 0.0583, wR2 (based on F2) = 0.1215, and GOF = 1.315 based on I > 2σ(I).
29. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1-S19.
30. + fragment: Munakata, M.; Kitagawa, S.; Kosome, S.; Asahara, A. Inorg. Chem. 1986, 25, 2622-2627.
31. (a) Turner, R. W.; Amma, E. L. J. Am. Chem. Soc. 1963, 85, 4046-4047.
32. (b) Dines, M. B.; Bird, P. H. J. Chem. Soc., Chem. Commun. 1973, 1, 12.
33. (c) Silverthorn, W. E. Adv. Organomet. Chem. 1975, 13, 47-137.
34. Full experimental details on the synthesis of ligands and the generation of the Cu(I) carbonyl complexes are provided in the Supporting Information.
35. For a recent example of metal carbonyl IR stretching frequencies as a measure of ligand electronics, see ref 7b.
36. Similar differences in stretching frequency have been reported between Cu(CO) complexes of fluorinated and nonfluorinated tris(pyrazolylborate) ligands: Rasika Dias, H. V.; Lu, H.-L. Inorg. Chem. 1995, 34, 5380-5382.
37. int = 0.0674). No absorption correction was applied. The least squares refinement converged normally with residuals of R (based on F) = 0.0444, wR2 (based on F2) = 0.1153, and GOF= 1.024 based on I > 2σ(I).
38. eff versus T (Figure S1).
39. Yokota, S.; Tachi, Y.; Itoh, S. Inorg. Chem. 2002, 41, 1342-1344.