Screening of a modular sugar-based phosphite-oxazoline ligand library in asymmetric Pd-catalyzed Heck reactions

Chemistry - A European Journal

Volumn 13, Issue 12, 2007, Pages 3296-3304

  Mata, Yvette ^a   Pàmies, Oscar ^a   Diéguez, Montserrat ^a  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

Author keywords

Asymmetric catalysis; Heck reaction; P,N ligands; Palladium

Indexed keywords

AMINES; CATALYSIS; MOLECULAR STRUCTURE; PALLADIUM; REACTION KINETICS;

ASYMMETRIC CATALYSIS; HECK REACTION;

SUGARS;

EID: 34250322758     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601714     Document Type: Article

References (37)

1. For recent reviews, see: a) L. T. Tietze, H. Ila, H. P. Bell, Chem. Rev. 2004, 104, 3453-3516;
2. b) L. X. Dai, T. Tu, S. L. You, W. P. Deng, X. L. Hou, Acc. Chem. Res. 2003, 36, 659-667;
3. c) C. Bolm, J. P. Hildebrand, K. Mun̈iz, N. Hermanns, Angew. Chem. 2001, 113, 3382-3407;
4. Angew. Chem. Int. Ed. 2001, 40, 3284-3308;
5. d) M. Shibasaki, E. M. Vogl in Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999, pp. 457-487;
6. e) O. Loiseleur, M. Hayashi, M. Keenan, N. Schemees, A. Pfaltz, J. Organomet, Chem. 1999, 576, 16-22;
7. f) M. Beller, T. H. Riermeier, O. Stark in Transition Metals for Organic Synthesis (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998, pp. 208-240.
8. See for instance: a) O. Loiseleur, P. Meier, A.: Pfaltz, Angew. Chem. 1996, 108, 218-220;
9. Angew. Chem. Int. Ed. Engl. 1996, 35, 200-202;
10. b) O. Loiseleur, M. Hayashi, N. Schmees, A. Pfaltz, Synthesis 1997, 1338-1345;
11. c) T. Tu, X. L. Hou, L. X. Dai, Org. Lett. 2003, 5, 3651-3653;
12. d) S. R. Gilbertson, D. Xie, Z. Fu, J. Org. Chem. 2001, 66, 7240-7246;
13. e) S. R. Gilbertson, Z. Fu, Org. Lett. 2001, 3, 161-164;
14. f) T. Tu, W. P. Deng, X. L. Hou, L. X. Dai, X. C. Dong, Chem. Eur. J. 2003, 9, 3073-3081;
15. g) S. R. Gilbertson, D. G. Genov, A. L. Rheingold, Org. Lett. 2000, 2, 2885-2888;
16. h) Y. Hashimoto, Y. Horie, M. Hayashi, K. Saigo, Tetrahedron: Asymmetry 2000, 11, 2205-2210;
17. i) X. L. Hou, D. X. Dong, K. Yuan, Tetrahedron: Asymmetry 2004, 15, 2189-2191;
18. j) D. Liu, Q. Dai, X. Zhang, Tetrahedron 2005, 61, 6460-6471.
19. See for instance: a) M. Diéguez, O. Pàmies, C. Claver, Chem. Rev. 2004, 104, 3189-3215;
20. b) M. Diéguez, O. Pàmies, A. Ruiz, Y. Díaz, S. Castillón, C. Claver, Coord. Chem. Rev. 2004, 248, 2165-2192;
21. c) M. Diéguez, A. Ruiz, C. Claver, Dalton Trans. 2003, 2957-2963;
22. d) O. Pàmies, M. Diéguez, A. Ruiz, C. Claver, Chem. Today 2004, 12-14;
23. e) M. Diéguez, O. Pàmies, A. Ruiz, C. Claver, in Methodologies in Asymmetric Catalysis (Ed.: S. V. Malhotra), American Chemical Society, Washington DC, 2004, pp. 161-173.
24. f) M. Diéguez, O. Pàmies, C. Claver, Tetrahedron: Asymmetry 2004, 15, 2113-2122.
25. a) G. P. F. van Strijdonck, M. D. K. Boele, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeuwen, Eur. J. Inorg. Chem. 1999, 1073-1076;
26. b) O. Pàmies, M. Diéguez, C. Claver, C. J. Am. Chem. Soc. 2005, 127, 3646-3647.
27. a) K. Yonehara, K. Mori, T. Hashizume, K. G. Chung, K. Ohe, S. Uemura, J. Organomet. Chem. 2000, 603, 40-49;
28. b) R. Imbos, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 2002, 124, 184-185.
29. The preliminary Heck results were partly reported in Y. Mata, M. Diéguez, O. Pàmies, C. Claver, Org. Lett. 2005, 7, 5597-5599. They represented the first application of phosphite-oxazoline ligands in this process.
30. K. Yonehara, T. Hashizume, K. Mori, K. Ohe, S. Uemura, J. Org. Chem. 1999, 64, 9374-9380.
31. O. Pàmies, M. Diéguez, G. Net, A. Ruiz, C. Claver, Organometallics 2000, 19, 1488-1496.
32. S. Takano, K. Dsmizu, K. Ogasawara. Synlett 1993, 393-394.
33. See for instance: Microwave Assisted Organic Synthesis (Eds.: J. P. Tierney, P. Lidström), Blackwell. 2005, and references therein.
34. P. Nilsson, H. Gold, M. Larhed, A. Hallberg, Synthesis 2002, 1611-1614.
35. a) G. J. H. Buisman, P. C. J. Kamer, P. W. N. M. van Leeuwen, Tetrahedron: Asymmetry 1993, 4, 1625-1634;
36. b) G. J. H. Buisman, L. A. van der Veen, A. Klootwijk, W. G. J. de Lange, P. C. J. Kamer, P. W. N. M. van Leeuwen, D. Vogt, Organometallics 1997, 16, 2929-2939.
37. Y. Mata, M. Diéguez, O. Pàmies, C. Claver, Adv. Synth. Catal. 2005, 347, 1943-1947.