Palladium-catalyzed α-arylation of tetramic acids

Journal of Organic Chemistry

Volumn 74, Issue 14, 2009, Pages 5032-5040

  Storgaard, Morten ^a,b   Dörwald, Florencio Zaragoza ^b,c   Peschke, Bernd ^b   Tanner, David ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b NOVO NORDISK A S   (Denmark)

^c LONZA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL CHLORIDE; ARYL HALIDES; ARYLATION; CHEMICAL EQUATIONS; CONVENTIONAL HEATING; ELECTRON DENSITIES; ELECTRON-RICH; ELECTROPHILE; GOOD YIELD; INDUCED HEATING; REACTION TIME; STERICALLY DEMANDING; TETRAMIC ACIDS; TRIFLATES;

AMINES; AMINO ACIDS; AROMATIC COMPOUNDS; BROMINE COMPOUNDS; CHEMICAL REACTIONS; CHLORINE COMPOUNDS; HEATING; ORGANIC ACIDS; PALLADIUM; PHOSPHORUS COMPOUNDS;

ELECTRONS;

2,4 PYRROLIDINEDIONE DERIVATIVE; BROMIDE; CHLORIDE; ELECTROPHILE; HALIDE; PALLADIUM; PHOSPHINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TETRAMIC ACID DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; ELECTRON TRANSPORT; HEATING; MICROWAVE RADIATION; RACEMIZATION; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY;

CATALYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PALLADIUM; PYRROLIDINONES;

EID: 67650401448     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900799y     Document Type: Article

References (43)

1. Mulholland, T. P. C.; Foster, R.; Haydock, D. B. J. Chem. Soc., Perkin Trans. 1 1972, 2121-2128.
2. Mulholland, T. P. C.; Foster, R.; Haydock, D. B. J. Chem. Soc., Perkin Trans. 1 1972, 1225-1231.
3. (a) Royles, B. J. L. Chem. Rev. 1995, 95, 1981-2001.
4. (b) Schobert, R.; Schlenk, A. Bioorg. Med. Chem. 2008, 16, 4203-4221.
5. Steyn, P. S.; Wessels, P. L. Tetrahedron Lett. 1978, 47, 4707-4710.
6. (a) Benary, E. Chem. Ber. 1907, 40, 1079-1083.
7. (b) Benary, E. Chem. Ber. 1911, 44, 1759-1765.
8. (a) Yamaguchi, H.; Nakayama, Y.; Takeda, K.; Tawara, K. J. Antibiot., Ser. A 1957, 10, 195-200.
9. (b) Fujimoto, H.; Kinoshita, T.; Suzuki, H.; Umezawa, H. J. Antibiot. 1970, 23, 271-275.
10. (c) Pettit, G. R.; Kamano, Y.; Dufresne, C.; Cerny, R. L.; Herald, C. L.; Schmidt, J. M. J. Org. Chem. 1989, 54, 6005-6006.
11. (d) Pettit, G. R.; Thornton, T. J.; Mullaney, J. T.; Boyd, M. R.; Herald, D. L.; Singh, S.-B.; Flahive, E. J. Tetrahedron 1994, 50, 12097-12108.
12. (e) Wright, A. D.; Osterhage, C.; König, G. M. Org. Biomol. Chem. 2003, 1, 507-510.
13. (a) Jouin, P.; Catro, B.; Nisato, D. J. Chem. Soc., Perkin Trans. 1 1987, 1177-1182.
14. (b) Schmidt, U.; Riedl, B.; Haas, G.; Griesser, H.; Vetter, A.; Weinbrenner, S. Synthesis 1993, 216-220.
15. (c) Fehrentz, J.-A.; Bourdel, E.; Califano, J.-C.; Chaloin, O.; Devin, C.; Garrouste, P.; Lima-Leite, A.-C.; Llinares, M.; Rieunier, F.; Vizavonna, J.; Winternitz, F.; Loffet, A.; Martinez, J. Tetrahedron Lett. 1994, 35, 1557-1560.
16. (d) Wittenberger, S. J.; Baker, W. R.; Donner, B. G.; Hutchins, C. W. Tetrahedron Lett. 1991, 32, 7655-7658.
17. (e) Hlubucek, J. R.; Lowe, G. J. Chem. Soc., Chem. Commun. 1974, 419-420.
18. (f) Rooney, C. S.; Randall, W. C.; Streeter, K. B.; Ziegler, C.; Cragoe, E. J., Jr.; Schwam, H.; Michelson, S. R.; Williams, H. W. R.; Eichler, E.; Duggan, D. E.; Ulm, E. H.; Noll, R. M. J. Med. Chem. 1983, 26, 700-714.
19. (g) Fischer, R.; Lehr, S.; Feucht, D.; Losel, P.; Malsam, O.; Bojack, G.; Auler, T.; Hills, M. J.; Kehne, H.; Rosinger, C. H. United States Patent Application Publication, US2007/0225167, September 27, 2007.
20. (a) Hosseini, M.; Kringelum, H.; Murray, A.; Tønder, J. E. Org. Lett. 2006, 8, 2103-2106.
21. (b) Hosseini, M.; Grau, J. S.; Sørensen, K. K.; Søtofte, I.; Tanner, D.; Murray, A.; Tønder, J. E. Org. Biomol. Chem. 2007, 5, 2207-2210.
22. (c) Hosseini, M.; Tanner, D.; Murray, A.; Tønder, J. E. Org. Biomol. Chem. 2007, 5, 3486-3494.
23. (a) Ma, D.; Ma, J.; Ding, W.; Dai, L. Tetrahedron: Asymmetry 1996, 7, 2365-2370.
24. (b) Courcambeck, J.; Bihel, F.; Michelis, C. D.; Quéléver, G.; Kraus, J. L. J. Chem. Soc., Perkin Trans. 1 2001, 1421-1430.
25. (a) Larsen, S.; Bernstein, J. J. Am. Chem. Soc. 1950, 72, 4447-4452.
26. (b) Andrews, M. D.; Brewster, A.; Moloney, M. G. Tetrahedron: Asymmetry 1994, 5, 1477-1478.
27. (c) Mawer, I. M.; Kulagowski, J. J.; Leeson, P. D.; Grimwood, S.; Marshall, G. R. Bioorg. Med. Chem. Lett. 1995, 5, 2643-2648.
28. (d) Matthews, J.; Rivero, R. A. J. Org. Chem. 1998, 63, 4808-4810.
29. Heckmann, J. Ann. Chem. 1883, 220, 128-146.
30. Bruggink, A.; McKillop, A. Tetrahedron 1975, 31, 2607-2619.
31. (a) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370.
32. (b) Terao, Y.; Fukuoka, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron Lett. 2002, 43, 101-104.
33. (c) Beare, N. A.; Hartwig, J. F. J. Org. Chem. 2002, 67, 541-555.
34. (d) Mitin, A. V.; Kashin, A. N.; Beletskaya, Russ. J. Org. Chem. 2004, 40, 802-812.
35. (e) Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2002, 41, 953-956.
36. (f) Hama, T.; Liu, X.; Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 11176-11177.
37. (g) Lee, S.; Beare, N. A.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 8410-8411.
38. (h) Filippis, A.; de Pardo, D. G.; Cossy, J. Tetrahedron 2004, 60, 9757-9767.
39. (i) Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234-245.
40. Schipper, D. J.; Campeau, L.-C.; Fagnou, K. Tetrahedron 2009, 65, 3155-3164.
41. Zhao, Y.; Zhou, Y.; Liang, L.; Yang, X.; Du, F.; Li, L.; Zhang, H. Org. Lett. 2009, 11, 555-558.
42. García-Fortanet, J.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 8108-8111.
43. Barder, T. E.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 5096-5101.