Mild room-temperature palladium-catalyzed C3-arylation of 2(1H)-pyrazinones via a desulfitative kumada-type cross-coupling reaction

Journal of Organic Chemistry

Volumn 74, Issue 17, 2009, Pages 6870-6873

  Mehta, Vaibhav P ^a   Modha, Sachin G ^a   Van Der Eycken, Erik ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; CHEMICAL EQUATIONS; CROSS COUPLING REACTIONS; CROSS-COUPLING PROTOCOL; ROOM TEMPERATURE; THIOESTERS; THIOETHERS;

CHEMICAL BONDS; CHEMICAL REACTIONS; PALLADIUM;

AROMATIC COMPOUNDS;

BENZENE DERIVATIVE; CHLORINE DERIVATIVE; ESTER DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRAZINE DERIVATIVE; SULFIDE;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CROSS COUPLING REACTION; REACTION ANALYSIS; REACTION TIME; ROOM TEMPERATURE; TECHNIQUE;

EID: 69549086681     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901327y     Document Type: Article

References (64)

1. (a) Transition Metals for Organic Synthesis, 2nd ed.; Bellar, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 2004.
2. (b) Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; Vols. 1 and 2.
3. (c) Beller, M.; Zapf, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., de Meijere, A., Eds.; Wiley: New York, 2002; Vol.1.
4. (a) Ley, S. V.; Thomas, A. W. Angew. Chem. 2003, 115, 5558;
5. (b) Angew. Chem., Int. Ed. 2003, 42, 5400.
6. (a) Tsuji, J. In Palladium Reagents and Catalysts: Innovations in Organic Synthesis;Wiley: Chichester, 1995.
7. (b) Tsuji, J. In Palladium in Organic Synthesis: Topics in Orgnaometallic Chemistry; Springer: New York, 2005.
8. (c) Lipshutz, B. H.; Sengupta, S. Org. React. 1992, 41, 135.
9. (d) Corriu, J. P.; Masse, J. P. J. Chem. Soc., Chem. Commun. 1972, 144.
10. (e) Duplais, C.; Bures, F.; Sapountzis, I.; Korn, T. J.; Cahiez, G.; Knochel, P. Angew. Chem. 2004, 116, 3028;
11. (j) Angew. Chem., Int. Ed. 2004, 43, 2968.
12. (f) Fürstner, A.; Leitner, A. Angew. Chem., Int. Ed. 2002, 41, 609 and ref erences cited therein.
13. (g) Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217.
14. (h) Taillefer, M.; Xia, N.; Ouali, A. Angew. Chem., Int. Ed., 2007, 47, 934 and references cited therein.
15. (i) Sherry, B. D.; Furstner, A. Acc. Chem. Res. 2008, 41, 1500.
16. (a) Saito, B.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 6694.
17. (b) Strotman, N. A.; Sommer, S.; Fu, G. C. Angew. Chem., Int. Ed. 2007, 46, 3556.
18. (c) Saito, B.; Fu, G. C. J. Am. Chem. Soc. 2007, 129, 9602.
19. (d) For a short review on non-activated alkyl halides, see: Frisch, A. C.; Beller, M. Angew. Chem. Int. Ed. 2005, 44, 674.
20. (a) Dubbaka, S. R.;Vogel, P. Angew. Chem. 2005, 117, 7848;
21. (b) Angew. Chem., Int. Ed. 2005, 44, 7674.
22. (a) Prokopkova, H.; Kappe, C. O. Angew. Chem., Int. Ed. 2009, 48, 2276 and references cited therein.
23. (b) Liebeskind, L. S.; Sorgl, J. J. Am. Chem. Soc. 2000, 122, 11260.
24. (c) Prokopkova, H.; Kappe, C. O. J. Org. Chem. 2007, 72, 4440.
25. (d) Miyura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
26. (e) Stille, J. K. Angew. Chem. 1986, 98, 504;
27. (i) Angew. Chem., Int. Ed. 1986, 25, 508.
28. (f ) Negshi, E.-i. Acc. Chem. Res. 1982, 15, 340.
29. (g) Mehta, V. P.; Sharma, A.; Van der Eycken, E. Adv. Synth. Catal. 2008, 350, 2174.
30. (a) Cahiez, G.; Foulgoc, L.; Moyeux, A. Angew. Chem., Int. Ed. 2009, 48, 2969.
31. (b) Cahiez, G.; Chaboche, C.; Duplais, C.; Moyeux, A. Org. Lett. 2009, 11, 277.
32. (c) Cahiez, G.; Moyeux, A.; Buendia, J.; Duplais, C. J. Am. Chem. Soc. 2007, 129, 13788.
33. (d) Knochel, P.; Krasovskiy, A.; Sapountzis, I. In Handbook of Functionalized Organometallics; Knochel, P., Ed.; Wiley-VCH: Weinheim, 2005; Vol.1, pp 109.
34. (a) Takahashi, T.; Kanno, K. I. In Modern Organonickel Chemistry; Tamaru, Y., Ed.; Wiley-VCH: Weinheim, 2005.
35. (b) Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374.
36. (c) Tamao, K.; Kiso, Y.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 9268.
37. (a) Lau, S. Y. W.; Hughes, G.; O'Shea, P. D.; Davies, I. W. Org. Lett. 2007, 9, 2239.
38. (b) Roques, N.; Saint-Jalmes, L. Tetrahedron Lett. 2006, 47, 3375.
39. (c) Wolf, J.; Labande, A.; Daran, J.-C.; Poli, R. J. Organomet. Chem. 2006, 691, 433.
40. Liang, L.-C.; Chien, P.-C.; Lin, J.-M.; Huang, M.-H.; Huang, Y.-L; Liao, J.-H. Organometallics 2006, 25, 1399-1411.
41. (e) Horibe, H.; Fukuda, Y.; Kondo, K.; Okuno, H.; Murakami, Y.; Aoyama, T. Tetrahedron 2004, 60, 10701.
42. (f) Yang, L.-M.; Huang, L.-F.; Luh, T.-Y. Org. Lett. 2004, 6, 1461.
43. Volla, C. M. R.; Vogel, P. Angew. Chem., Int. Ed. 2008, 47, 1305.
44. (a) Wenkert, E.; Shepard, M. E.; Mcphail, A. T. J. Chem. Soc., Chem. Commun. 1986, 1390.
45. (b) Wenkert, E.; Fernandes, J. B.; Michelotti, E. L.; Swindell, C. S. Synthesis 1983, 701.
46. (c) Wenkert, E.; Ferreira, T. W.; Michelotti, E. L. J. Chem. Soc., Chem. Commun. 1979, 637.
47. (a) Okamura, H.; Miura, M.; Takei, H. Tetrahedron Lett. 1979, 1, 43.
48. (b) Okamura, H.; Takei, H. Tetrahedron Lett. 1979, 36, 3425.
49. (a) Kumada, M. Pure Appl. Chem. 1980, 52, 669.
50. (b) Walla, P.; Kappe, C. O. Chem. Commun. 2004, 564.
51. (c) Xi, Z.; Liu, B.; Chen, W. J. Org. Chem. 2008, 73, 3954.
52. Itami, K.; Mineno, M.; Muraoka, N.; Yoshida, J.-i. J. Am. Chem. Soc. 2004, 126, 11778.
53. (a) Appukkuttan, P.; Van der Eycken, E. Eur. J. Org. Chem. 2008, 1133.
54. (b) Topics in Heterocyclic Chemistry; Van der Eycken, E., Kappe, C. O., Eds.; Springer Verlag: Berlin, 2006; Vol.1, p 267.
55. (a) Kaval, N.; Bisztray, K.; Dehaen, W.; Kappe, C. O.; Van der Eycken, E. Molecular Diversity 2003, 7, 125.
56. (b) Singh, B. K.; Parmar, V. S.; Van der Eycken, E. Synlett 2008, 3021.
57. (c) Mehta, V. P.; Sharma, A.; Van der Eycken, E. Org. Lett. 2008, 10, 1147.
58. (d) Sharma, A.; Mehta, V. P.; Van der Eycken, E. Tetrahedron 2008, 64, 2605.
59. (e) Singh, B. K.; Mehta, V. P.; Parmar, V. S.; Van der Eycken, E. Org. Biomol. Chem. 2007, 5, 2962.
60. (f ) Kaval, N.; Singh, B. K.; Ermolat'ev, D. S.; Claerhout, S.; Van der Eycken, J.; Van der Eycken, E. J. Comb. Chem. 2007, 9, 446.
61. Venkatesh, C.; Singh, B.; Mahata, P. K.; Ila, H.; Junjappa, H. Org. Lett. 2005, 7, 2169.
62. (a) Martin, R.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3844.
63. (b) Ackermann, L.; Althammer, A. Org. Lett. 2006, 8, 3457.
64. We preferred to use aryl-, heteroaryl-, and alkylmagnesium bromides instead of magnesium chlorides as the latter are insufficiently reactive.