Tunable carbon-carbon and carbon-sulfur cross-coupling of boronic acids with 3,4-dihydropyrimidine-2-thiones

Organic Letters

Volumn 6, Issue 5, 2004, Pages 771-774

  Lengar, Alenka ^a   Kappe, C Oliver ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; CARBON; COPPER DERIVATIVE; KETONE DERIVATIVE; PYRIMIDINE DERIVATIVE; SULFUR;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION; COMPLEX FORMATION; CROSS COUPLING REACTION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 1642360667     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036496h     Document Type: Article

References (36)

1. (a) Diedrich, F.; Stang, P. J., Eds. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, 1998.
2. (b) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
3. (a) Tyrell, E.; Brookes, P. Synthesis 2003, 469.
4. (b) Miyaura, N. Top. Curr. Chem. 2002, 279, 11.
5. (c) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
6. Suzuki, A.; Miyaura, N. Chem. Rev. 1995, 95, 2457.
7. (a) Ishiyama, T.; Kizaki, H.; Hayashi, T.; Suzuki, A.; Miyaura, N. J. Org. Chem. 1998, 63, 4726.
8. (b) Lautens, M.; Roy, A.; Fukuoka, K.; Fagnou, K.; Martin-Matute, B. J. Am. Chem. Soc. 2001, 123, 5358.
9. Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937.
10. (a) Herradura, P. S.; Pendola, K. A.; Guy, R. K. Org. Lett. 2000, 2, 2019.
11. (b) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4, 4309.
12. (a) Bakkestuen, A. K.; Gundersen, L.-L. Tetrahedron Lett. 2003, 44, 3359.
13. (b) Combs, A. P.; Saubern, S.; Rafalski, M.; Lam, P. Y. S. Tetrahedron Lett. 1999, 40, 1623.
14. (a) Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 722, 11260.
15. (b) Liebeskind, L. S.; Srogl, J. Org. Lett. 2002, 4, 979.
16. (c) Kusturin, C. L.; Liebeskind, L. S.; Neumann, W. L. Org. Lett. 2002, 4, 983.
17. (d) See also: Alphonse, F.-A.; Suzenet, F.; Keromnes, A.; Lebret, B.; Guillaumet, G. Synlett 2002, 447.
18. For related, non-boronic acid couplings, see: (a) Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5, 801. (b) Wittenberg, R.; Srogl, J.; Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5, 3033. (c) Alphonse, F.-A.; Suzenet, F.; Keromnes, A. ; Lebret, B.; Guillaumet, G. Org. Lett. 2003, 5, 803.
19. For related, non-boronic acid couplings, see: (a) Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5, 801. (b) Wittenberg, R.; Srogl, J.; Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5, 3033. (c) Alphonse, F.-A.; Suzenet, F.; Keromnes, A. ; Lebret, B.; Guillaumet, G. Org. Lett. 2003, 5, 803.
20. For related, non-boronic acid couplings, see: (a) Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5, 801. (b) Wittenberg, R.; Srogl, J.; Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5, 3033. (c) Alphonse, F.-A.; Suzenet, F.; Keromnes, A. ; Lebret, B.; Guillaumet, G. Org. Lett. 2003, 5, 803.
21. Kusturin, C.; Liebeskind, L. S.; Rahman, H.; Sample, K.; Schweitzer, B.; Srogl, J.; Neumann, W. L. Org. Lett. 2003, 5, 4349.
22. For reviews, see: (a) Kappe, C. O. Acc. Chem. Res. 2000, 33, 879. (b) Kappe, C. O. QSAR Comb. Sci. 2003, 22, 622.
23. For reviews, see: (a) Kappe, C. O. Acc. Chem. Res. 2000, 33, 879. (b) Kappe, C. O. QSAR Comb. Sci. 2003, 22, 622.
24. Deres, K.; Schröder, C. H.; Paessens, A.; Goldmann, S.; Hacker, H. J.; Weber, O.; Kraemer, T.; Niewoehner, U.; Pleiss, U.; Stoltefuss, J.; Graef, E.; Koletzki, D.; Masantschek, R. N. A.; Reimann, A.; Jaeger, R.; Groß, R.; Beckermann, B.; Schlemmer, K.-H.; Haebich, D.; Rübsamen-Waigmann, H. Science 2003, 299, 893.
25. (a) Kappe, C. O.; Roschger, P. J. Heterocycl. Chem. 1989, 26, 55.
26. (b) Atwal, K.; Rovnyak, G. C.; Schwartz, J.; Moreland, S.; Hedberg, A.; Gougoutas, J. Z.; Malley, M. F.; Floyd, D. M. J. Med. Chem. 1990, 33, 1510.
27. For a recent review, see the following: Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717. (b) For general references on microwave-assisted organic synthesis, see: Microwave-Assisted Organic Synthesis (MAOS) Webpages. http://www.maos.net.
28. For a recent review, see the following: Larhed, M.; Moberg, C.; Hallberg, A. Acc. Chem. Res. 2002, 35, 717. (b) For general references on microwave-assisted organic synthesis, see: Microwave-Assisted Organic Synthesis (MAOS) Webpages. http://www.maos.net.
29. (a) Kuno, A.; Sugiyama, Y.; Katsuta, K.; Kamitani, T.; Takasugi, H. Chem. Pharm. Bull. 1992, 40, 1452.
30. (b) Weis, A. L. Synthesis 1985, 528.
31. For the rapid synthesis of combinatorial libraries of these heterocycles employing microwave-assisted solution-phase methods, see: Stadler, A.; Kappe, C. O. J. Comb. Chem. 2001, 3, 624.
32. When the same reaction was run in an oil bath under conventional reflux conditions (ca 65 °C, reflux temperature, 18 h), the desired product 2a was also formed but in significantly lower yield (ca. 40-50%).
33. Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295.
34. For a review of Cu-Mediated C-O, C-N, and C-S bond-forming reactions of the Ullmann type, see: ref 2c.
35. -1; MS (pos. APCI): m/z 321 (M + 1).
36. Dondoni, A.; Massi, A.; Sabatini, S. Tetrahedron Lett. 2002, 43, 5913.