Palladium(0)-catalyzed, copper(I)-mediated coupling of cyclic thioamides with alkenylboronic acids, organostannanes, and siloxanes

Journal of Organic Chemistry

Volumn 74, Issue 14, 2009, Pages 5118-5121

  Arshad, Nuzhat ^a   Hashim, Jamshed ^a   Kappe, C Oliver ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLSTANNANES; COFACTOR; CROSS-COUPLING; CROSS-COUPLING PROTOCOL; CROSS-COUPLINGS; GOOD YIELD; HETEROCYCLIC STRUCTURES; MULTIMODE; NEUTRAL CONDITIONS; ORGANOSTANNANES; PARALLEL REACTIONS; SINGLE MODE; THIOAMIDE; THIOAMIDES;

ACIDS; MICROWAVE IRRADIATION; SILICON COMPOUNDS; THIOUREAS; UREA;

PALLADIUM;

1,4 DIHYDROPYRIMIDINE DERIVATIVE; ALKENYL GROUP; BORONIC ACID DERIVATIVE; CUPROUS ION; DIHYDROPYRIMIDINE DERIVATIVE; PALLADIUM; PYRIMIDINE DERIVATIVE; SILOXANE; THIOAMIDE; TIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CATALYSIS; CROSS COUPLING REACTION; DRUG ACTIVITY; DRUG SYNTHESIS; HEATING; MICROWAVE IRRADIATION; REACTION ANALYSIS;

EID: 67650355485     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900848s     Document Type: Article

References (30)

1. Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260.
2. (a) Liebeskind, L. S.; Srogl, J. Org. Lett. 2002, 4, 979.
3. (b) Kusturin, C. L.; Liebeskind, L. S.; Neumann, W. L. Org. Lett. 2002, 4, 983.
4. (c) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3, 91.
5. (d) Yang, H.; Li, H.; Wittenberg, R.; Egi, M.; Huang, W.; Liebeskind, L. S. J. Am. Chem. Soc. 2007, 129, 1132.
6. (a) Kusturin, C.; Liebeskind, L. S.; Rahman, H.; Sample, K.; Schweitzer, B.; Srogl, J.; Neumann, W. L. Org. Lett. 2003, 5, 4349.
7. (b) Aguilar-Aguilar, A.; Peña-Cabrera, E. Org. Lett. 2007, 9, 4163.
8. (a) Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5, 801.
9. (b) Wittenberg, R.; Srogl, J.; Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5, 3033.
10. (c) Alphonse, F.-A.; Suzenet, F.; Keromnes, A.; Lebret, B.; Guillaumet, G. Org. Lett. 2003, 5, 803.
11. (d) Leconte, N.; Pellegatti, L.; Tatibouët, A.; Suzenet, F.; Rollin, P.; Guillaumet, G. Synthesis 2007, 857.
12. (e) Li, H.; Yang, H.; Liebeskind, L. S. Org. Lett. 2008, 10, 4375.
13. Mehta, V. P.; Sharma, A.; Van der Eycken, E. Adv. Synth. Catal. 2008, 350, 2174.
14. (a) Mehta, V. P.; Sharma, A.; Van der Eycken, E. Org. Lett. 2008, 10, 1147.
15. (b) Shook, B. C.; Charkravarty, D.; Jackson, P. F. Tetrahedron Lett. 2009, 50, 1013.
16. For a review on the Liebeskind-Srogl reaction, see: Prokopcová, H.; Kappe, C. O. Angew. Chem., Int. Ed. 2009, 48, 2276.
17. Lengar, A.; Kappe, C. O. Org. Lett. 2004, 6, 771.
18. (a) Prokopcová, H.; Kappe, C. O. Adv. Synth. Catal. 2007, 349, 448.
19. (b) Prokopcová, H.; Kappe, C. O. J. Org. Chem. 2007, 72, 4440.
20. The use of linear substrates in all of our examples (refs 8 and 9) did not provide any of the desired coupling products.
21. For the use of alkenylboronic acids in the Liebeskind-Srogl reaction, see: Yang, H.; Liebeskind, L. S. Org. Lett. 2007, 9, 2993.
22. Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250.
23. Deres, K.; Schröder, C. H.; Paessens, A.; Goldmann, S.; Hacker, H. J.; Weber, O.; Krämer, 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.
24. Stadler, A.; Kappe, C. O. J. Comb. Chem. 2001, 3, 624.
25. Attempted cross-coupling of thioamides with alkylboronic acids (cyclohexylboronic acid and 2-phenyl-1-ethylboronic acid) or boronic esters (phenylboronic acid pinacol- and propane diol ester) was unsuccessful.
26. (a) Damm, M.; Kappe, C. O. J. Comb. Chem. 2009, 11, 460.
27. (a) Silva, S.; Tardy, S.; Routier, S.; Suzenet, F.; Tatibouët, A.; Rauter, A. P.; Rollin, P. Tetrahedron Lett. 2008, 49, 5583.
28. (b) For related cross-couplings using terminal alkynes, see: Silva, S.; Sylla, B.; Suzenet, F.; Tatibouët, A.; Rauter, A. P.; Rollin, P. Org. Lett. 2008, 10, 853.
29. (a) Hiyama, T. J. Organomet. Chem. 2002, 653, 58.
30. (b) Denmark, S. E. Aldrichim. Acta 2003, 36, 75.