Novel three-component reactions based on a heck carbopalladation/ cyclization domino reaction

Angewandte Chemie - International Edition

Volumn 43, Issue 44, 2004, Pages 5997-6000

  Kressierer, Christoph J ^a   Müller, Thomas J J ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Amination; C C coupling; Domino reactions; Multicomponent reactions; Olefination

Indexed keywords

ESTERS; FURAN RESINS; HALIDE MINERALS; PALLADIUM COMPOUNDS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CARBOPALLADATION; TETRAHYDROFURANS; THREE-COMPONENT REACTIONS;

REACTION KINETICS;

ALCOHOL DERIVATIVE; ESTER DERIVATIVE; PALLADIUM COMPLEX; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; DOMINO REACTION; ISOMERIZATION; REACTION ANALYSIS; SOLID; SYNTHESIS;

ALCOHOLS; AMINATION; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PALLADIUM;

EID: 9244231752     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461134     Document Type: Article

References (35)

1. For excellent reviews, see for example, a) E.-I. Negishi, C. Copéret, S. Ma, S.-Y. Liou, F. Liu, Chem. Rev. 1996, 96, 365;
2. b) M. Malacria, Chem. Rev. 1996, 96, 289;
3. c) S. Bräse, A. de Meijere in Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, 1998, p. 99.
4. For recent reviews on transition-metal-catalyzed reactions in heterocyclic synthesis, see for example, a) G. Kirsch, S. Hesse, A. Cornel, Curr. Org. Synth. 2004, 1, 47;
5. b) I. Nakamura, Y. Yamamoto, Chem. Rev. 2004, 104, 2127, and references therein;
6. c) For a monograph on heterocycle synthesis by means of palladium-catalyzed reactions, see for example, J. J. Lie, G. W. Gribble, Palladium in Heterocyclic Chemistry, Pergammon, Oxford, 2000.
7. a) H. Bienaymé, C. Hulme, G. Oddon, P. Schmitt, Chem. Eur. J. 2000, 6, 3321;
8. b) I. Ugi, A. Dömling, B. Werner, J. Heterocycl. Chem. 2000, 37, 647;
9. c) L. Weber, K. Illgen, M. Almstetter, Synlett 1999, 366;
10. d) G. H. Posner, Chem. Rev. 1986, 86, 831.
11. For recent excellent reviews on transition-metal-assisted sequential transformations and domino processes, see for example, a) G. Balme, E. Bossharth, N. Monteiro, Eur. J. Org. Chem. 2003, 4101;
12. b) G. Battistuzzi, S. Cacchi, G. Fabrizi, Eur. J. Org. Chem. 2002, 2671;
13. c) L. F. Tietze, Chem. Rev. 1996, 96, 115.
14. S. Kobayashi, Chem. Soc. Rev. 1999, 28, 1.
15. a) A. S. Karpov, T. Oeser, T. J. J. Müller, Chem. Commun. 2004, 1502;
16. b) A. S. Karpov, F. Rominger, T. J. J. Müller, J. Org. Chem. 2003, 68, 1503;
17. c) N. A. M. Yehia, K. Polborn, T. J. J. Müller, Tetrahedron Lett. 2002, 43, 6907;
18. d) R. U. Braun, K. Zeitler, T. J. J. Müller, Org. Lett. 2001, 3, 3297;
19. e) T. J. J. Müller, J. P. Robert, E. Schmälzlin, C. Bräuchle, K. Meerholz, Org. Lett. 2000, 2, 2419;
20. f) T. J. J. Müller, M. Ansorge, D. Aktah, Angew. Chem. 2000, 112, 1323; Angew. Chem. Int. Ed. 2000, 39, 1253.
21. f) T. J. J. Müller, M. Ansorge, D. Aktah, Angew. Chem. 2000, 112, 1323; Angew. Chem. Int. Ed. 2000, 39, 1253.
22. a) C. J. Kressierer, T. J. J. Müller, Tetrahedron Lett. 2004, 45, 2155;
23. b) C. J. Kressierer, T. J. J. Müller, Synlett 2004, 655.
24. J. T. Link, L. E. Overman in Metal-Catalyzed Cross-Coupling Reactions, Wiley-VCH, Weinheim, 1998, p. 231.
25. For a review, see for example, a) B. M. Trost, Acc. Chem. Res. 1990, 23, 34;
26. b) B. M. Trost, J. Dumas, M. Villa, J. Am. Chem. Soc. 1992, 114, 9836;
27. c) B. M. Trost, J. Dumas, J. Am. Chem. Soc. 1992, 114, 1924;
28. d) S. Brown, S. Clarkson, R. Grigg, V. Sridharan, Tetrahedron Lett. 1993, 34, 157.
29. X. Xie, X. Lu, Tetrahedron Lett. 1999, 40, 8415.
30. The syntheses of alkynylallyl alcohol substrates were performed according to H. Sajiki, K. Hirota, Tetrahedron 1998, 54, 13981. The detailed protocols will be described elsewhere.
31. All compounds were fully characterized spectroscopically and provided either correct elemental analysis or HRMS.
32. a) T. Jeffery, Tetrahedron Lett. 1990, 31, 6641;
33. b) S. A. Buntin, R. F. Heck, Org. Synth. Coll. Vol. 1990, 7, 361.
34. For reviews, see for example, a) M. L. Moore, Org. React. 1949, 5, 301;
35. b) A. Lukasiewicz, Tetrahedron 1963, 19, 1789.