Intramolecular Pd-mediated processes of amino-tethered aryl halides and ketones: Insight into the ketone α-arylation and carbonyl-addition dichotomy. A new class of four-membered azapalladacycles

Journal of the American Chemical Society

Volumn 125, Issue 6, 2003, Pages 1587-1594

  Solé, Daniel ^a   Vallverdú, Lluís ^a   Solans, Xavier ^a   Font Bardía, Mercè ^a   Bonjoch, Josep ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AMINES; CATALYST ACTIVITY; HALOGEN COMPOUNDS; KETONES; X RAY ANALYSIS;

ARYLATION;

CHEMICAL ENGINEERING;

ALKANONE; AMINE; CARBONYL DERIVATIVE; HALIDE; KETONE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; ARYLATION; CHEMICAL REACTION; REACTION ANALYSIS; X RAY ANALYSIS;

EID: 0037433240     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029114w     Document Type: Article

References (72)

1. Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry: A Guide for the Synthetic Chemist; Pergamon: Amsterdam, 2000.
2. For some examples in which the coordination of N with the metal controls or modifies the course of transition metal promoted processes, see: (a) Oestreich, M.; Dennison, P. R.; Kodanko, J. J.; Overman, L. E. Angew. Chem., Int. Ed. 2001, 40, 1439-1442. (b) Mauleón, P.; Alonso, I.; Carretero, J. C. Angew. Chem., Int. Ed. 2001, 40, 1291-1293. (c) Olofsson, K.; Sahlin, H.; Larhed, M.; Hallberg, A. J. Org. Chem. 2001, 66, 544-549. (d) Solé, D.; Cancho, Y.; Llebaria, A.; Moretó, J. M.; Delgado, A. J. Am. Chem. Soc. 1994, 116, 12133-12134.
3. For some examples in which the coordination of N with the metal controls or modifies the course of transition metal promoted processes, see: (a) Oestreich, M.; Dennison, P. R.; Kodanko, J. J.; Overman, L. E. Angew. Chem., Int. Ed. 2001, 40, 1439-1442. (b) Mauleón, P.; Alonso, I.; Carretero, J. C. Angew. Chem., Int. Ed. 2001, 40, 1291-1293. (c) Olofsson, K.; Sahlin, H.; Larhed, M.; Hallberg, A. J. Org. Chem. 2001, 66, 544-549. (d) Solé, D.; Cancho, Y.; Llebaria, A.; Moretó, J. M.; Delgado, A. J. Am. Chem. Soc. 1994, 116, 12133-12134.
4. For some examples in which the coordination of N with the metal controls or modifies the course of transition metal promoted processes, see: (a) Oestreich, M.; Dennison, P. R.; Kodanko, J. J.; Overman, L. E. Angew. Chem., Int. Ed. 2001, 40, 1439-1442. (b) Mauleón, P.; Alonso, I.; Carretero, J. C. Angew. Chem., Int. Ed. 2001, 40, 1291-1293. (c) Olofsson, K.; Sahlin, H.; Larhed, M.; Hallberg, A. J. Org. Chem. 2001, 66, 544-549. (d) Solé, D.; Cancho, Y.; Llebaria, A.; Moretó, J. M.; Delgado, A. J. Am. Chem. Soc. 1994, 116, 12133-12134.
5. For some examples in which the coordination of N with the metal controls or modifies the course of transition metal promoted processes, see: (a) Oestreich, M.; Dennison, P. R.; Kodanko, J. J.; Overman, L. E. Angew. Chem., Int. Ed. 2001, 40, 1439-1442. (b) Mauleón, P.; Alonso, I.; Carretero, J. C. Angew. Chem., Int. Ed. 2001, 40, 1291-1293. (c) Olofsson, K.; Sahlin, H.; Larhed, M.; Hallberg, A. J. Org. Chem. 2001, 66, 544-549. (d) Solé, D.; Cancho, Y.; Llebaria, A.; Moretó, J. M.; Delgado, A. J. Am. Chem. Soc. 1994, 116, 12133-12134.
6. Solé, D.; Peidró, E.; Bonjoch, J. Org. Lett. 2000, 2, 2225-2228.
7. For reactions starting from ketones, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383. (c) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473-1478. (d) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370. (e) Terao, Y.; Kametani, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2001, 57, 5967-5974. (f) Mutter, R.; Campbell, I. B.; Martin de la Nava, E. M.; Merritt, A. T.; Wills, M. J. Org. Chem. 2001, 66, 3284-3290. (g) Hamada, T.; Chieffi, A.; Ahman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261-1268. (h) Ehrentraut, A.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2002, 344, 209-217. (i) Churruca, F.; SanMartin, R.; Tellitu, I.; Domínguez E. Org. Lett. 2002, 4, 1591-1594. (j) Viciu, M. S.; Germaneau, R. F.; Nolan, S. P. Org. Lett. 2002, 4, 4053-4056.
8. For reactions starting from ketones, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383. (c) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473-1478. (d) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370. (e) Terao, Y.; Kametani, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2001, 57, 5967-5974. (f) Mutter, R.; Campbell, I. B.; Martin de la Nava, E. M.; Merritt, A. T.; Wills, M. J. Org. Chem. 2001, 66, 3284-3290. (g) Hamada, T.; Chieffi, A.; Ahman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261-1268. (h) Ehrentraut, A.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2002, 344, 209-217. (i) Churruca, F.; SanMartin, R.; Tellitu, I.; Domínguez E. Org. Lett. 2002, 4, 1591-1594. (j) Viciu, M. S.; Germaneau, R. F.; Nolan, S. P. Org. Lett. 2002, 4, 4053-4056.
9. For reactions starting from ketones, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383. (c) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473-1478. (d) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370. (e) Terao, Y.; Kametani, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2001, 57, 5967-5974. (f) Mutter, R.; Campbell, I. B.; Martin de la Nava, E. M.; Merritt, A. T.; Wills, M. J. Org. Chem. 2001, 66, 3284-3290. (g) Hamada, T.; Chieffi, A.; Ahman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261-1268. (h) Ehrentraut, A.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2002, 344, 209-217. (i) Churruca, F.; SanMartin, R.; Tellitu, I.; Domínguez E. Org. Lett. 2002, 4, 1591-1594. (j) Viciu, M. S.; Germaneau, R. F.; Nolan, S. P. Org. Lett. 2002, 4, 4053-4056.
10. For reactions starting from ketones, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383. (c) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473-1478. (d) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370. (e) Terao, Y.; Kametani, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2001, 57, 5967-5974. (f) Mutter, R.; Campbell, I. B.; Martin de la Nava, E. M.; Merritt, A. T.; Wills, M. J. Org. Chem. 2001, 66, 3284-3290. (g) Hamada, T.; Chieffi, A.; Ahman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261-1268. (h) Ehrentraut, A.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2002, 344, 209-217. (i) Churruca, F.; SanMartin, R.; Tellitu, I.; Domínguez E. Org. Lett. 2002, 4, 1591-1594. (j) Viciu, M. S.; Germaneau, R. F.; Nolan, S. P. Org. Lett. 2002, 4, 4053-4056.
11. For reactions starting from ketones, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383. (c) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473-1478. (d) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370. (e) Terao, Y.; Kametani, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2001, 57, 5967-5974. (f) Mutter, R.; Campbell, I. B.; Martin de la Nava, E. M.; Merritt, A. T.; Wills, M. J. Org. Chem. 2001, 66, 3284-3290. (g) Hamada, T.; Chieffi, A.; Ahman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261-1268. (h) Ehrentraut, A.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2002, 344, 209-217. (i) Churruca, F.; SanMartin, R.; Tellitu, I.; Domínguez E. Org. Lett. 2002, 4, 1591-1594. (j) Viciu, M. S.; Germaneau, R. F.; Nolan, S. P. Org. Lett. 2002, 4, 4053-4056.
12. For reactions starting from ketones, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383. (c) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473-1478. (d) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370. (e) Terao, Y.; Kametani, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2001, 57, 5967-5974. (f) Mutter, R.; Campbell, I. B.; Martin de la Nava, E. M.; Merritt, A. T.; Wills, M. J. Org. Chem. 2001, 66, 3284-3290. (g) Hamada, T.; Chieffi, A.; Ahman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261-1268. (h) Ehrentraut, A.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2002, 344, 209-217. (i) Churruca, F.; SanMartin, R.; Tellitu, I.; Domínguez E. Org. Lett. 2002, 4, 1591-1594. (j) Viciu, M. S.; Germaneau, R. F.; Nolan, S. P. Org. Lett. 2002, 4, 4053-4056.
13. For reactions starting from ketones, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383. (c) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473-1478. (d) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370. (e) Terao, Y.; Kametani, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2001, 57, 5967-5974. (f) Mutter, R.; Campbell, I. B.; Martin de la Nava, E. M.; Merritt, A. T.; Wills, M. J. Org. Chem. 2001, 66, 3284-3290. (g) Hamada, T.; Chieffi, A.; Ahman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261-1268. (h) Ehrentraut, A.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2002, 344, 209-217. (i) Churruca, F.; SanMartin, R.; Tellitu, I.; Domínguez E. Org. Lett. 2002, 4, 1591-1594. (j) Viciu, M. S.; Germaneau, R. F.; Nolan, S. P. Org. Lett. 2002, 4, 4053-4056.
14. For reactions starting from ketones, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383. (c) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473-1478. (d) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370. (e) Terao, Y.; Kametani, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2001, 57, 5967-5974. (f) Mutter, R.; Campbell, I. B.; Martin de la Nava, E. M.; Merritt, A. T.; Wills, M. J. Org. Chem. 2001, 66, 3284-3290. (g) Hamada, T.; Chieffi, A.; Ahman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261-1268. (h) Ehrentraut, A.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2002, 344, 209-217. (i) Churruca, F.; SanMartin, R.; Tellitu, I.; Domínguez E. Org. Lett. 2002, 4, 1591-1594. (j) Viciu, M. S.; Germaneau, R. F.; Nolan, S. P. Org. Lett. 2002, 4, 4053-4056.
15. For reactions starting from ketones, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383. (c) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473-1478. (d) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370. (e) Terao, Y.; Kametani, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2001, 57, 5967-5974. (f) Mutter, R.; Campbell, I. B.; Martin de la Nava, E. M.; Merritt, A. T.; Wills, M. J. Org. Chem. 2001, 66, 3284-3290. (g) Hamada, T.; Chieffi, A.; Ahman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261-1268. (h) Ehrentraut, A.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2002, 344, 209-217. (i) Churruca, F.; SanMartin, R.; Tellitu, I.; Domínguez E. Org. Lett. 2002, 4, 1591-1594. (j) Viciu, M. S.; Germaneau, R. F.; Nolan, S. P. Org. Lett. 2002, 4, 4053-4056.
16. For reactions starting from ketones, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108-11109. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383. (c) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473-1478. (d) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370. (e) Terao, Y.; Kametani, Y.; Wakui, H.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron 2001, 57, 5967-5974. (f) Mutter, R.; Campbell, I. B.; Martin de la Nava, E. M.; Merritt, A. T.; Wills, M. J. Org. Chem. 2001, 66, 3284-3290. (g) Hamada, T.; Chieffi, A.; Ahman, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1261-1268. (h) Ehrentraut, A.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2002, 344, 209-217. (i) Churruca, F.; SanMartin, R.; Tellitu, I.; Domínguez E. Org. Lett. 2002, 4, 1591-1594. (j) Viciu, M. S.; Germaneau, R. F.; Nolan, S. P. Org. Lett. 2002, 4, 4053-4056.
17. For reactions starting from aldehydes, see: Terao, Y.; Fukuoka, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron Lett. 2002, 43, 101-104.
18. For reactions starting from esters, see: Moradi, W. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7996-8002. Lee, S.; Beare, N. A.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 8410-8411. Jorgensen, M.; Lee, S.; Liu, X.; Wolkowski, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 12557-12565.
19. For reactions starting from esters, see: Moradi, W. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7996-8002. Lee, S.; Beare, N. A.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 8410-8411. Jorgensen, M.; Lee, S.; Liu, X.; Wolkowski, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 12557-12565.
20. For reactions starting from esters, see: Moradi, W. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7996-8002. Lee, S.; Beare, N. A.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 8410-8411. Jorgensen, M.; Lee, S.; Liu, X.; Wolkowski, J. P.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 12557-12565.
21. For reactions starting from amides, see: Shaughnessy, K. H.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1998, 63, 6546-6553.
22. 8c see: (a) Beare, N. A.; Hartwig, J. F. J. Org. Chem. 2002, 67, 541-555. Kashin, A. N.; Mitin, A. V.; Beletskaya, I. P.; Wife, R. Tetrahedron Lett. 2002, 43, 2539-2542. Aramendía, M. A.; Borau, V.; Jiménez, C.; Marinas, J. M.; Ruiz, J. R.; Urbano, F. J. Tetrahedron Lett. 2002, 43, 2847-2849. Kondo, Y.; Inamoto, K.; Uchiyama, M.; Sakamoto, T. Chem. Commun. 2001, 2704-2705. See also ref 4c. (b) Vogl, E. M.; Buchwald, S. L. J. Org. Chem. 2002, 67, 106-111. (c) Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9330-9331.
23. 8c see: (a) Beare, N. A.; Hartwig, J. F. J. Org. Chem. 2002, 67, 541-555. Kashin, A. N.; Mitin, A. V.; Beletskaya, I. P.; Wife, R. Tetrahedron Lett. 2002, 43, 2539-2542. Aramendía, M. A.; Borau, V.; Jiménez, C.; Marinas, J. M.; Ruiz, J. R.; Urbano, F. J. Tetrahedron Lett. 2002, 43, 2847-2849. Kondo, Y.; Inamoto, K.; Uchiyama, M.; Sakamoto, T. Chem. Commun. 2001, 2704-2705. See also ref 4c. (b) Vogl, E. M.; Buchwald, S. L. J. Org. Chem. 2002, 67, 106-111. (c) Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9330-9331.
24. 8c see: (a) Beare, N. A.; Hartwig, J. F. J. Org. Chem. 2002, 67, 541-555. Kashin, A. N.; Mitin, A. V.; Beletskaya, I. P.; Wife, R. Tetrahedron Lett. 2002, 43, 2539-2542. Aramendía, M. A.; Borau, V.; Jiménez, C.; Marinas, J. M.; Ruiz, J. R.; Urbano, F. J. Tetrahedron Lett. 2002, 43, 2847-2849. Kondo, Y.; Inamoto, K.; Uchiyama, M.; Sakamoto, T. Chem. Commun. 2001, 2704-2705. See also ref 4c. (b) Vogl, E. M.; Buchwald, S. L. J. Org. Chem. 2002, 67, 106-111. (c) Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9330-9331.
25. 8c see: (a) Beare, N. A.; Hartwig, J. F. J. Org. Chem. 2002, 67, 541-555. Kashin, A. N.; Mitin, A. V.; Beletskaya, I. P.; Wife, R. Tetrahedron Lett. 2002, 43, 2539-2542. Aramendía, M. A.; Borau, V.; Jiménez, C.; Marinas, J. M.; Ruiz, J. R.; Urbano, F. J. Tetrahedron Lett. 2002, 43, 2847-2849. Kondo, Y.; Inamoto, K.; Uchiyama, M.; Sakamoto, T. Chem. Commun. 2001, 2704-2705. See also ref 4c. (b) Vogl, E. M.; Buchwald, S. L. J. Org. Chem. 2002, 67, 106-111. (c) Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9330-9331.
26. 8c see: (a) Beare, N. A.; Hartwig, J. F. J. Org. Chem. 2002, 67, 541-555. Kashin, A. N.; Mitin, A. V.; Beletskaya, I. P.; Wife, R. Tetrahedron Lett. 2002, 43, 2539-2542. Aramendía, M. A.; Borau, V.; Jiménez, C.; Marinas, J. M.; Ruiz, J. R.; Urbano, F. J. Tetrahedron Lett. 2002, 43, 2847-2849. Kondo, Y.; Inamoto, K.; Uchiyama, M.; Sakamoto, T. Chem. Commun. 2001, 2704-2705. See also ref 4c. (b) Vogl, E. M.; Buchwald, S. L. J. Org. Chem. 2002, 67, 106-111. (c) Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9330-9331.
27. 8c see: (a) Beare, N. A.; Hartwig, J. F. J. Org. Chem. 2002, 67, 541-555. Kashin, A. N.; Mitin, A. V.; Beletskaya, I. P.; Wife, R. Tetrahedron Lett. 2002, 43, 2539-2542. Aramendía, M. A.; Borau, V.; Jiménez, C.; Marinas, J. M.; Ruiz, J. R.; Urbano, F. J. Tetrahedron Lett. 2002, 43, 2847-2849. Kondo, Y.; Inamoto, K.; Uchiyama, M.; Sakamoto, T. Chem. Commun. 2001, 2704-2705. See also ref 4c. (b) Vogl, E. M.; Buchwald, S. L. J. Org. Chem. 2002, 67, 106-111. (c) Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9330-9331.
28. Ciufolini, M. A.; Qi, H.-B.; Browne, M. E. J. Org. Chem. 1988, 53, 4149-4151.
29. Muratake, H.; Natsume, M. Tetrahedron Lett. 1997, 38, 7581-7582.
30. For the Pd-catalyzed intramolecular coupling of aryl halides and aldehyde enolates, see: Muratake, H.; Nakai, H. Tetrahedron Lett. 1999, 40, 2355-2358.
31. Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402-3415.
32. (a) Freund, R.; Mederski, W. W. K. R. Helv. Chim. Acta 2000, 83, 1247-1255.
33. (b) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 193-195.
34. (c) Zhang, T. Y.; Zhang, H. Tetrahedron Lett. 2002, 43, 1363-1365.
35. For the extension of the α-arylation of amides to the synthesis of δ-lactams, see: Honda, T.; Namiki, H.; Satoh, F. Org. Lett. 2001, 3, 631-633.
36. Gaertzen, O.; Buchwald, S. L. J. Org. Chem. 2002, 67, 465-475.
37. Solé, D.; Vallverdú, L.; Bonjoch, J. Adv. Synth. Catal. 2001, 343, 439-442.
38. Staub, G. M.; Gloer, J. B.; Dowd, P. F.; Wicklow, D. T. J. Am. Chem. Soc. 1992, 114, 1015-1017.
39. Quetin-Leclercq, J.; Angenot, L.; Dupont, L.; Dideberg, O.; Warin, R.; Delaude, C.; Coune, C. Tetrahedron Lett. 1991, 32, 4295-4298.
40. The failure of the cyclization of acetanilide 3 under these reaction conditions might be attributed to the acid hydrogens of the acetamido group. In fact, the Pd-catalyzed intramolecular α-arylation of 2-haloacetanilides using NaOt-Bu as the base has been reported; see refs 7 and 12.
41. The formation of hydrodehalogenation byproducts has been reported; see for example refs 7, 10, and 14.
42. For a preliminary account of part of our studies with ω-(2-haloanilino) alkanones, see: Solé, D.; Vallverdú, L.; Peidró, E.; Bonjoch, J. Chem. Commun. 2001, 1888-1889.
43. For example, under reaction conditions of method A, β-anilino ketones 11a and 18, and α-anilino ketones 29 and 32, afforded N-benzylaniline as the only isolable product.
44. The intramolecular addition of aryl palladium halides to ketones is an uncommon transformation that has not been described until very recently, see: Quan, L. G.; Lamrani, M.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 4827-4828.
45. 24d see: (a) Quan, L. G.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 3545-3546. (b) Vicente, J.; Abad, J.-A.; López-Peláez, B.; Martínez-Viviente, E. Organometallics 2002, 21, 58-67. (c) Larock, R. C.; Doty, M. J.; Cacchi, S. J. Org. Chem. 1993, 58, 4579-4583. Gevorgyan, V.; Quan, L. G.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4089-4092. (d) Larock, R. C.; Tian, Q.; Pletnev, A. A. J. Am. Chem. Soc. 1999, 121, 3238-3239.
46. 24d see: (a) Quan, L. G.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 3545-3546. (b) Vicente, J.; Abad, J.-A.; López-Peláez, B.; Martínez-Viviente, E. Organometallics 2002, 21, 58-67. (c) Larock, R. C.; Doty, M. J.; Cacchi, S. J. Org. Chem. 1993, 58, 4579-4583. Gevorgyan, V.; Quan, L. G.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4089-4092. (d) Larock, R. C.; Tian, Q.; Pletnev, A. A. J. Am. Chem. Soc. 1999, 121, 3238-3239.
47. 24d see: (a) Quan, L. G.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 3545-3546. (b) Vicente, J.; Abad, J.-A.; López-Peláez, B.; Martínez-Viviente, E. Organometallics 2002, 21, 58-67. (c) Larock, R. C.; Doty, M. J.; Cacchi, S. J. Org. Chem. 1993, 58, 4579-4583. Gevorgyan, V.; Quan, L. G.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4089-4092. (d) Larock, R. C.; Tian, Q.; Pletnev, A. A. J. Am. Chem. Soc. 1999, 121, 3238-3239.
48. 24d see: (a) Quan, L. G.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 3545-3546. (b) Vicente, J.; Abad, J.-A.; López-Peláez, B.; Martínez-Viviente, E. Organometallics 2002, 21, 58-67. (c) Larock, R. C.; Doty, M. J.; Cacchi, S. J. Org. Chem. 1993, 58, 4579-4583. Gevorgyan, V.; Quan, L. G.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4089-4092. (d) Larock, R. C.; Tian, Q.; Pletnev, A. A. J. Am. Chem. Soc. 1999, 121, 3238-3239.
49. 24d see: (a) Quan, L. G.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 3545-3546. (b) Vicente, J.; Abad, J.-A.; López-Peláez, B.; Martínez-Viviente, E. Organometallics 2002, 21, 58-67. (c) Larock, R. C.; Doty, M. J.; Cacchi, S. J. Org. Chem. 1993, 58, 4579-4583. Gevorgyan, V.; Quan, L. G.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4089-4092. (d) Larock, R. C.; Tian, Q.; Pletnev, A. A. J. Am. Chem. Soc. 1999, 121, 3238-3239.
50. Wender, P. A.; White, A. W. Tetrahedron 1983, 39, 3767-3776.
51. Especially interesting is the preparation of the novel benzazepine 38, whose use in the synthesis of Crinane-type alkaloids is now being studied.
52. Aromatization of existing rings is an important means of synthesis of isoindoles, see: Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 2, pp 119-206.
53. It is interesting to note that on standing in solution isoquinoline 40 partially oxidizes to isoquinolone 41.
54. 11 The formation of the carbonyl arylation compounds was explained by means of the insertion of σ-arylpalladium species into the formyl C-H bond, a reaction that is not possible from ketones.
55. 23 reveals that the substitution pattern of the majority prevents the α-arylation reaction from taking place.
56. 2Ar protons, and all of the protons of the palladated aromatic ring are between δ 6 and 7. These NMR data are very different from those recorded for the azapalladacycles 46 and 47 (see the Supporting Information).
57. These reactions were carried out without precautions against the presence of moisture. So, as long reactions times are required, adventitious water could account for the formation of the hydroxopalladium(II) complexes. For the formation of hydroxopalladium complexes, see: (a) Getty, A. D.; Goldberg, K. I. Organometallics 2001, 20, 2545-2551. Matos, K.; Soderquist, J. A. J. Org. Chem. 1998, 63, 461-470.
58. hese reactions were carried out without precautions against the presence of moisture. So, as long reactions times are required, adventitious water could account for the formation of the hydroxopalladium(II) complexes. For the formation of hydroxopalladium complexes, see: (a) Getty, A. D.; Goldberg, K. I. Organometallics 2001, 20, 2545-2551. Matos, K.; Soderquist, J. A. J. Org. Chem. 1998, 63, 461-470.
59. It is interesting to note that the N atom could play an important role in the formation of these hydroxopalladium complexes because they have not been observed during the preparation of the bis(triphenylphosphane)palladium complexes of the non-nitrogen-containing haloaryl ketones. So. the hydrolysis reaction could occur by deprotonation by the amino group of the more acidic coordinated water. For a related process, see: Albéniz, A. C.; Espinet, P.; Manrique, R.; Pérez-Mateo, A. Angew. Chem., Int. Ed. 2002, 41, 2363-2366.
60. Detailed crystallographic and spectroscopic data of 46 and 48 are provided in the Supporting Information.
61. Allen, F. H.; Kennard, O. Chem. Des. Autom. News 1993, 8, 31-37.
62. For a recent review: Dupont, J.; Pfeffer, M.; Spencer, J. Eur. J. Inorg. Chem. 2001, 1917-1927.
63. Vicente, J.; Abad, J.-A.; Frankland, A. D.; Ramírez de Arellano, M. C. Chem.-Eur. J. 1999, 5, 3066-3075.
64. 3 and dba.
65. 4.
66. The coordination ability of intramolecular ketone carbonyl groups has already been observed: Vicente, J.; Abad, J.-A.; Martínez-Viviente, E.; Ramírez de Arellano, M. C.; Jones, P. G. Organometallics 2000, 19, 752-760.
67. We agree with the reviewer who suggests that the formation of the C=O chelated intermediate could take place via a pentacoordinated Pd(II) complex (not illustrated in Figure 4). For a related proposal, see: Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488-6499.
68. The carbopalladation reaction probably requires an eclipsed arrangement that may not be likely when n = 3. See: Overman, L. E.; Abelman, M. M.; Kucera, D. J.; Tran, V. D.; Ricca, D. J. Pure Appl. Chem. 1992, 64, 1813-1819.
69. For the isolation and study of the reductive elimination reaction of aryl palladium enolates, see: Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 5816-5817.
70. 4 directly afforded alcohols 27-cis and 27-trans, although in moderate yields.
71. 3N (entries 3-19, Table 2), no γ-butyrolactone was obtained. It is known that tertiary amines with α-hydrogens could be the reductants in Pd-catalyzed reactions, see: Stokker, G. E. Tetrahedron Lett. 1987, 28, 3179-3182. Murahashi, S.-I.; Hirano, T.; Yano, T. J. Am. Chem. Soc. 1978, 100, 348-350.
72. 3N (entries 3-19, Table 2), no γ-butyrolactone was obtained. It is known that tertiary amines with α-hydrogens could be the reductants in Pd-catalyzed reactions, see: Stokker, G. E. Tetrahedron Lett. 1987, 28, 3179-3182. Murahashi, S.-I.; Hirano, T.; Yano, T. J. Am. Chem. Soc. 1978, 100, 348-350.