Synthesis of ketones from α-oxocarboxylates and aryl bromides by Cu/Pd-catalyzed decarboxylative cross-coupling

Angewandte Chemie - International Edition

Volumn 47, Issue 16, 2008, Pages 3043-3045

  Gooßen, Lukas J ^a   Rudolphi, Felix ^a   Oppel, Christoph ^a   Rodríguez, Nuria ^a  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

Aryl ketones; Copper; Cross coupling; Homogeneous catalysis; Palladium

Indexed keywords

ACIDS; BROMINE COMPOUNDS; CARBOXYLATION; CHEMICAL REACTIONS; FUNCTIONAL GROUPS; KETONES; SYNTHESIS (CHEMICAL);

ARYL KETONES; COPPER; CROSS-COUPLING; HOMOGENEOUS CATALYSIS; PALLADIUM;

ORGANIC COMPOUNDS;

BROMIDE; CARBOXYLIC ACID; COPPER; CROSS LINKING REAGENT; KETONE; PALLADIUM;

ARTICLE; CATALYSIS; DECARBOXYLATION; SYNTHESIS;

BROMIDES; CARBOXYLIC ACIDS; CATALYSIS; COPPER; CROSS-LINKING REAGENTS; DECARBOXYLATION; KETONES; PALLADIUM;

EID: 44949096668     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705127     Document Type: Article

References (33)

1. a) P. J. Masson, D. Coup, J. Millet, N. L. Brown, J. Biol. Chem. 1994, 270, 2662-2668;
2. b) K. R. Romines, G. A. Freeman, L. T. Schaller, J. R. Cowan, S. S. Gonzales, J. H. Tidwell, C. W. Andrews, D. K. Stammers, R. J. Hazen, R. G. Ferris, S. A. Short, J. H. Chan, L. R. Boone, J. Med. Chem. 2006, 49, 727-739.
3. C. W. Schellhammer in Methoden der Organischen Chemie (Houben-Weyl), Volume VII/2a (Ed.: E. Müller), Thieme, Stuttgart, 1973, p. 15-379.
4. J. Cason, J. Am. Chem. Soc. 1942, 64, 1106-1110.
5. S. Nahm, S. M. Weinreb, Tetrahedron Lett. 1981, 22, 3815-3818.
6. E. Negishi, F. Liu in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, p. 18-19.
7. a) E. Negishi, V. Bagheri, S. Chatterjee, F. T. Luo, J. A. Miller, A. T. Stoll, Tetrahedron Lett. 1983, 24, 5181-5184;
8. b) P. Knochel, M. C. P. Yeh, S. C. Berk, J. Talbert, J. Org. Chem. 1988, 53, 2392-2394.
9. M. Haddach, J. R. McCarthy, Tetrahedron Lett. 1999, 40, 3109-3112.
10. a) L. J. Gooßen, K. Ghosh, Angew. Chem. 2001, 113, 3566-3568;
11. Angew. Chem. Int. Ed. 2001, 40, 3458-3460;
12. b) L. J. Gooßen, K. Ghosh, Eur. J. Org. Chem. 2002, 3254-3267;
13. c) L. J. Gooßen, L. Winkel, A. Döhring, K. Ghosh, J. Paetzold, Synlett 2002, 1237-1240.
14. L. J. Gooßen, K. Ghosh, Chem. Commun. 2001, 2084-2085.
15. E. J. Corey, D. Seebach, Angew. Chem. 1965, 77, 1134-1135;
16. Angew. Chem. Int. Ed. Engl. 1965, 4, 1075-1077.
17. a) G. Stork, L. Maldonado, J. Am. Chem. Soc. 1971, 93, 5286-5287;
18. b) R. E. Damon, R. H. Schlessinger, Tetrahedron Lett. 1975, 16, 4551-4554;
19. c) D. Seebach, Angew. Chem. 1969, 81, 690-700;
20. Angew. Chem. Int. Ed. Engl. 1969, 8, 639-649;
21. d) R. M. Adlington, J. E. Baldwin, J. C. Bottaro, M. W. D. Perry, J. Chem. Soc. Chem. Commun. 1983, 1040-1041.
22. A. Takemiya, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 14800-14801.
23. a) Y. C. Huang, K. K. Majumdar, C. H. Cheng, J. Org. Chem. 2002, 67, 1682- 1684;
24. b) S. Ko, B. Kang, S. Chang, Angew. Chem. 2005, 117, 459-461;
25. Angew. Chem. Int. Ed. 2005, 44, 455-457.
26. a) L. J. Gooßen, G. Deng, L. M. Levy, Science 2006, 313, 662-664;
27. b) L. J. Gooßen, N. Rodríguez, B. Melzer, C. Linder, G. Deng, L. M. Levy, J. Am. Chem. Soc. 2007, 129, 4824-4833.
28. L. J. Gooßen, W. R. Thiel, N. Rodríguez, C. Linder, B. Melzer, Adv. Synth. Catal. 2007, 349, 2241-2246.
29. Decarboxylation of α-oxocarboxylic acids: a) A. Claus, R. Wollner, Ber. Dtsch. Chem. Ges. 1885, 18, 1856-1861;
30. b) T. Cohen, I. H. Song, J. Am. Chem. Soc. 1965, 87, 3780-3781.
31. Synthesis of acylcuprates from organolithium compounds: D. Seyferth, R. C. Hui, J. Am. Chem. Soc. 1985, 107, 4551-4553.
32. W. A. Herrmann, C. Brossmer, K. Öfele, C. P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989-1992;
33. Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1848.