Palladium-catalyzed intramolecular nucleophilic substitution at the alkoxycarbonyl group

Angewandte Chemie - International Edition

Volumn 46, Issue 38, 2007, Pages 7270-7272

  Solé, Daniel ^a   Serrano, Olga ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Acylation; Cyclization; Nitrogen heterocycles; Nucleophilic substitution; Palladium

Indexed keywords

NITROGEN HETEROCYCLES; NUCLEOPHILIC SUBSTITUTION; ORGANOPALLADIUM REAGENTS;

ACYLATION; CATALYSIS; CYCLIZATION; ESTERS; NITROGEN COMPOUNDS; PALLADIUM;

SUBSTITUTION REACTIONS;

ALCOHOL DERIVATIVE; ALKOXY RADICAL; ORGANOMETALLIC COMPOUND; PALLADIUM; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; CHEMISTRY;

ACYLATION; ALCOHOLS; CATALYSIS; ORGANOMETALLIC COMPOUNDS; PALLADIUM;

EID: 34948900486     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200702176     Document Type: Article

References (37)

1. Handbook of Organopalladium Chemistry for Organic Synthesis, Vols. I and II (Ed.: E. Negishi), Wiley-VCH, New York, 2002.
2. For the reaction of aryl and vinyl palladium complexes with aldehydes, see: a) R. C. Larock, M. J. Doty, S. Cacchi, J. Org. Chem. 1993, 58, 4579-4583;
3. b) V. Gevorgyan, L. G. Quan, Y. Yamamoto, Tetrahedron Lett. 1999, 40, 4089-4092;
4. c) L. Zhao, X. Lu, Angew. Chem. 2002, 114, 4519-4521;
5. Angew. Chem. Int. Ed. 2002, 41, 4343-4345;
6. d) J. Vicente, J.-A. Abad, B. López-Peláez, E. Martínez-Viviente, Organometallics 2002, 21, 58-67.
7. For the reaction of aryl and vinyl palladium complexes with ketones, see: a) L. G. Quan, V. Gevorgyan, Y. Yamamoto, J. Am. Chem. Soc. 1999, 121, 3545-3546:
8. b) L. G. Quan, M. Lamrani, Y. Yamamoto, J. Am. Chem. Soc. 2000, 122, 4827-4828;
9. c) D. Solé, L. Vallverdú, X. Solans, M. Font-Bardia, J. Bonjoch, J. Am. Chem. Soc. 2003, 125, 1587-1594;
10. d) G. Liu, X. Lu, J. Am. Chem. Soc. 2006, 128, 16504-16505; see also ref. [2c-d].
11. For the reaction of aryl palladium complexes with acetic anhydride, see: S. Cacchi, G. Fabrizi, F. Gavazza, A. Goggiamani, Org. Lett. 2003, 5, 289-291.
12. For the reaction of aryl and vinyl palladium complexes with nitriles, see: a) C.-C. Yang, P.-J. Sun, J.-M. Fang, J. Chem. Soc. Chem. Commun. 1994, 2629-2630;
13. b) R. C. Larock, Q. Tian, A. A. Pletnev, J. Am. Chem. Soc. 1999, 121, 3238-3239;
14. c) A. A. Pletnev, Q. Tian, R. C. Larock, J. Org. Chem. 2002, 67, 9276-9287;
15. d) A. A. Pletnev, R. C. Larock, J. Org. Chem. 2002, 67, 9428-9438;
16. e) Q. Tian, A. A. Pletnev, R. C. Larock, J. Org. Chem. 2003, 68, 339-347;
17. f) C. Zhou, R. C. Larock, J. Am. Chem. Soc. 2004, 126, 2302-2303;
18. g) C. Zhou, R. C. Larock, J. Org. Chem. 2006, 71, 3551-3558;
19. h) B. Zhao, X. Lu, Tetrahedron Lett. 2006, 47, 6765-6768; see also ref. [2c].
20. The few Pd-mediated reactions in which an ester functionality is modified do not involve the carbopalladation of the carbonyl group; see, for example: a) W. Tao, L. J. Silverberg, A. L. Rheingold, R. F. Heck, Organometallics 1989, 8, 2550-2559;
21. b) R. C. Larock, X. Han, M. J. Doty, Tetrahedron Lett. 1998, 39, 5713-5716.
22. For recent reviews, see: a) G. C. Lloyd-Jones, Angew. Chem. 2002, 114, 995-998;
23. Angew. Chem. Int. Ed. 2002, 41, 953-956;
24. b) D. A. Culkin, J. F. Hartwig, Acc. Chem. Res. 2003, 36, 234-245.
25. a) W. A. Moradi, S. L. Buchwald, J. Am. Chem. Soc. 2001, 123, 7996-8002;
26. b) S. Lee, N. A. Beare, J. F. Hartwig, J. Am. Chem. Soc. 2001, 123, 8410-8411;
27. c) M. Jorgensen, S. Lee, X. Liu, J. P. Wolkowski, J. F. Hartwig, J. Am. Chem. Soc. 2002, 124, 12557-12565:
28. d) T. Hama, X. Liu, D. A. Culkin, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 11176- 11177;
29. e) X. Liu, J. F. Hartwig, J. Am. Chem. Soc. 2004, 126, 5182-5191.
30. O. Gaertzen, S. L. Buchwald, J. Org. Chem. 2002, 67, 465-475.
31. a) A. B. Daruwala, J. E. Gearien, W. J. Dunn III, P. S. Benoit, L. Bauer, J. Med. Chem. 1974, 17, 819-824;
32. b) K. Nishijima, T. Shinkawa, Y. Yamashita, N. Sato, H. Nishida, K. Kato, Y. Onuki, M. Mizota, K. Ohmoto, S. Miyano, Eur. J. Med. Chem. 1998, 33, 267-277.
33. The reduction is a common side reaction in such processes; see, for example, refs. [3b,c,5d].
34. 0-catalyzed intramolecular coupling of amino-tethered vinyl halides with esters also proceeds without any interference from nucleophilic attack at the ester group; the addition of a phenoxide to the reaction mixture is necessary to promote the reaction at the α position; see: D. Solé, X. Urbaneja, J. Bonjoch, Adv. Synth. Catal. 2004, 346, 1646-1650.
35. For a related rhodium(I)-catalyzed transformation, see: T. Miura, T. Sasaki, H. Nakazawa, M. Murakami, J. Am. Chem. Soc. 2005, 127, 1390-1391.
36. II, see: S. Gosiewska, M. Huis in't Veld, J. J. M. de Pater, P. C. A. Bruijnincx, M. Lutz, A. L. Spek, G. van Koten, R. J. M. Klein Gebbink, Tetrahedron: Asymmetry 2006, 17, 674-686.
37. 3N) can not be excluded completely; see: S.-I. Murahashi, T. Hirano, T. Yano, J. Am. Chem. Soc. 1978, 100, 348-350.