Lewis acidity expressed in neutral electron-rich aluminum(III) complexes: An example of ligand-defined catalysis [12]

Journal of the American Chemical Society

Volumn 122, Issue 38, 2000, Pages 9318-9319

  Nelson, Scott G ^a   Kim, Beon Kyu ^a   Peelen, Timothy J ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALDEHYDE; ALUMINUM DERIVATIVE; AMINE; KETENE DERIVATIVE; LEWIS ACID; N,N DIMETHYLFORMAMIDE; UNCLASSIFIED DRUG;

CATALYST; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; ELECTRON; GEOMETRY; LETTER; MOLECULAR DYNAMICS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STRUCTURE ANALYSIS; X RAY DIFFRACTION;

EID: 0034721449     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja002415q     Document Type: Letter

References (34)

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10. Triamine complexes: (a) Emig, N.; Nguyen, H.; Krautscheid, H.; Reau, R.; Cazaux, J.-B.; Bertrand, G. Organometallics 1998, 17, 3599. (b) Emig, N.; Gabbaï, F. P.; Krautsheid, H.; Réau, R.; Bertrand, G. Angew. Chem. Int. Ed. Engl. 1998, 37, 989. Emig, N.; Réau, R.; Krautscheid, H.; Fenske, D.; Bertrand, G. J. Am. Chem. Soc. 1996, 118, 5822. Tetraamine complexes: (d) Pinkas, J.; Wang, T.; Jacobsen, R. A.; Verkade, J. G. Inorg. Chem. 1994, 33, 4202. (e) Pinkas, J.; Gaul, B.; Verkade, J. G. J. Am. Chem. Soc. 1993, 115, 3925. See also: (f) Müller, J.; Englert, U. Chem. Ber. 1995, 128, 493.
11. Triamine complexes: (a) Emig, N.; Nguyen, H.; Krautscheid, H.; Reau, R.; Cazaux, J.-B.; Bertrand, G. Organometallics 1998, 17, 3599. (b) Emig, N.; Gabbaï, F. P.; Krautsheid, H.; Réau, R.; Bertrand, G. Angew. Chem. Int. Ed. Engl. 1998, 37, 989. Emig, N.; Réau, R.; Krautscheid, H.; Fenske, D.; Bertrand, G. J. Am. Chem. Soc. 1996, 118, 5822. Tetraamine complexes: (d) Pinkas, J.; Wang, T.; Jacobsen, R. A.; Verkade, J. G. Inorg. Chem. 1994, 33, 4202. (e) Pinkas, J.; Gaul, B.; Verkade, J. G. J. Am. Chem. Soc. 1993, 115, 3925. See also: (f) Müller, J.; Englert, U. Chem. Ber. 1995, 128, 493.
12. Triamine complexes: (a) Emig, N.; Nguyen, H.; Krautscheid, H.; Reau, R.; Cazaux, J.-B.; Bertrand, G. Organometallics 1998, 17, 3599. (b) Emig, N.; Gabbaï, F. P.; Krautsheid, H.; Réau, R.; Bertrand, G. Angew. Chem. Int. Ed. Engl. 1998, 37, 989. Emig, N.; Réau, R.; Krautscheid, H.; Fenske, D.; Bertrand, G. J. Am. Chem. Soc. 1996, 118, 5822. Tetraamine complexes: (d) Pinkas, J.; Wang, T.; Jacobsen, R. A.; Verkade, J. G. Inorg. Chem. 1994, 33, 4202. (e) Pinkas, J.; Gaul, B.; Verkade, J. G. J. Am. Chem. Soc. 1993, 115, 3925. See also: (f) Müller, J.; Englert, U. Chem. Ber. 1995, 128, 493.
13. Triamine complexes: (a) Emig, N.; Nguyen, H.; Krautscheid, H.; Reau, R.; Cazaux, J.-B.; Bertrand, G. Organometallics 1998, 17, 3599. (b) Emig, N.; Gabbaï, F. P.; Krautsheid, H.; Réau, R.; Bertrand, G. Angew. Chem. Int. Ed. Engl. 1998, 37, 989. Emig, N.; Réau, R.; Krautscheid, H.; Fenske, D.; Bertrand, G. J. Am. Chem. Soc. 1996, 118, 5822. Tetraamine complexes: (d) Pinkas, J.; Wang, T.; Jacobsen, R. A.; Verkade, J. G. Inorg. Chem. 1994, 33, 4202. (e) Pinkas, J.; Gaul, B.; Verkade, J. G. J. Am. Chem. Soc. 1993, 115, 3925. See also: (f) Müller, J.; Englert, U. Chem. Ber. 1995, 128, 493.
14. Nucleophilic additions: (a) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (b) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1997, 119, 5754. Radical additions: (c) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713. Cycloadditions: (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jøgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Heller, D. P.; Goldberg, D. R.; Wulff, W. D. J. Am. Chem. Soc. 1997, 119, 10551. Conjugate additions: (f) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. HCN additions: (g) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315.
15. Nucleophilic additions: (a) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (b) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1997, 119, 5754. Radical additions: (c) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713. Cycloadditions: (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jøgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Heller, D. P.; Goldberg, D. R.; Wulff, W. D. J. Am. Chem. Soc. 1997, 119, 10551. Conjugate additions: (f) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. HCN additions: (g) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315.
16. Nucleophilic additions: (a) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (b) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1997, 119, 5754. Radical additions: (c) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713. Cycloadditions: (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jøgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Heller, D. P.; Goldberg, D. R.; Wulff, W. D. J. Am. Chem. Soc. 1997, 119, 10551. Conjugate additions: (f) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. HCN additions: (g) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315.
17. Nucleophilic additions: (a) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (b) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1997, 119, 5754. Radical additions: (c) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713. Cycloadditions: (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jøgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Heller, D. P.; Goldberg, D. R.; Wulff, W. D. J. Am. Chem. Soc. 1997, 119, 10551. Conjugate additions: (f) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. HCN additions: (g) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315.
18. Nucleophilic additions: (a) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (b) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1997, 119, 5754. Radical additions: (c) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713. Cycloadditions: (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jøgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Heller, D. P.; Goldberg, D. R.; Wulff, W. D. J. Am. Chem. Soc. 1997, 119, 10551. Conjugate additions: (f) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. HCN additions: (g) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315.
19. Nucleophilic additions: (a) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (b) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1997, 119, 5754. Radical additions: (c) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713. Cycloadditions: (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jøgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Heller, D. P.; Goldberg, D. R.; Wulff, W. D. J. Am. Chem. Soc. 1997, 119, 10551. Conjugate additions: (f) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. HCN additions: (g) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315.
20. Nucleophilic additions: (a) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1998, 120, 5327. (b) Ooi, T.; Uraguchi, D.; Kagoshima, N.; Maruoka, K. J. Am. Chem. Soc. 1997, 119, 5754. Radical additions: (c) Murakata, M.; Jono, T.; Mizuno, Y.; Hoshino, O. J. Am. Chem. Soc. 1997, 119, 11713. Cycloadditions: (d) Simonsen, K. B.; Svenstrup, N.; Roberson, M.; Jøgensen, K. A. Chem. Eur. J. 2000, 6, 123. (e) Heller, D. P.; Goldberg, D. R.; Wulff, W. D. J. Am. Chem. Soc. 1997, 119, 10551. Conjugate additions: (f) Arai, T.; Sasai, H.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 1998, 120, 441. HCN additions: (g) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315.
21. Nelson, S. G.; Peelen, T. J.; Wan, Z. J. Am. Chem. Soc. 1999, 121, 9742.
22. Negishi, E. Chem Eur. J. 1999, 5, 411.
23. 1H NMR as the catalyst resting state during these cyclocondensation reactions. See ref 5.
24. 2, 23 °C) results in no exchange of the bound DMF indicating that carbonyl coordination to 1 is irreversible under these conditions.
25. Ketene was generated in situ from acetyl bromide and Hünig's base using the reaction conditions described in ref 5.
26. -4.
27. Using 10 mol % 4, the acetyl bromide-hydrocinnamaldehyde test reaction proceeds to ∼20% conversion over 8 h but does not turn over.
28. 1H NMR.
29. Geometry optimization was performed using the Spartan molecular dynamics package utilizing the PM3 parameters. This parameter set provided a close match between the X-ray structure of 1 and the geometry optimized structure obtained using Spartan. Thus, this parameter set was considered to provide the most representative geometry of Al(III) complex 5.
30. Efforts to obtain an X-ray structure of 5 were unsuccessful.
31. Reacting complex 5 with excess DMF, even at elevated temperatures, failed to elicit formation of a Lewis acid-base adduct. This observation is indicative of the large energetic barrier that would accompany accessing a pentacoordinate complex derived from 5.
32. 4-amine complexes plays a crucial role in the ligand acceleration characteristic of these reactions. For leading references to extensive research on this topic, see: (a) Pidun, U.; Boehme, C.; Frenking, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1917. (b) Torrent, M.; Deng, L.; Duran, M.; Sola, M.; Ziegler, T. Organometallics 1997, 16, 13. Norrby, P.-O.; Rasmussen, T.; Haller, J.; Strassner, T.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 10188.
33. 4-amine complexes plays a crucial role in the ligand acceleration characteristic of these reactions. For leading references to extensive research on this topic, see: (a) Pidun, U.; Boehme, C.; Frenking, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1917. (b) Torrent, M.; Deng, L.; Duran, M.; Sola, M.; Ziegler, T. Organometallics 1997, 16, 13. Norrby, P.-O.; Rasmussen, T.; Haller, J.; Strassner, T.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 10188.
34. 4-amine complexes plays a crucial role in the ligand acceleration characteristic of these reactions. For leading references to extensive research on this topic, see: (a) Pidun, U.; Boehme, C.; Frenking, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1917. (b) Torrent, M.; Deng, L.; Duran, M.; Sola, M.; Ziegler, T. Organometallics 1997, 16, 13. Norrby, P.-O.; Rasmussen, T.; Haller, J.; Strassner, T.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 10188.