Mild, base-free copper-catalyzed N-arylations of heterocycles using potassium aryltrifluoroborates in water under air

Tetrahedron Letters

Volumn 51, Issue 22, 2010, Pages 2994-2997

  Joubert, Nicolas ^a   Baslé, Emmanuel ^a   Vaultier, Michel ^a   Pucheault, Mathieu ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

Boron; Copper; N Arylation; Trifluoro(organo)borates

Indexed keywords

CHEMICAL COMPOUND; COPPER; HETEROCYCLIC COMPOUND; IMIDAZOLE; POTASSIUM ARYLTRIFLUOROBORATE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMOREACTIVITY; HUMIDITY; IRRADIATION; PURIFICATION; REACTION TIME; SYNTHESIS; TEMPERATURE;

TRIFLUORO;

EID: 77951228252     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.118     Document Type: Article

References (47)

1. Goldberg I. Ber. Deutsch. Chem. Gesell. 39 (1906) 1691-1696
2. Ackermann L. In: Ackermann L. (Ed). Modern Arylation Methods (2009), Wiley-VCH Verlag GmbH
3. Ullmann F. Ber. Deutsch. Chem. Gesell. 36 (1903) 2382-2384
4. Yang B.H., and Buchwald S.L. J. Organomet. Chem. 576 (1999) 125-146
5. Corbet J.-P., and Mignani G. Chem. Rev. 106 (2006) 2651-2710
6. Ma D., and Cai Q. Acc. Chem. Res. 41 (2008) 1450-1460
7. Evano G., Blanchard N., and Toumi M. Chem. Rev. 108 (2008) 3054-3131
8. Monier F., and Taillefer M. Angew. Chem., Int. Ed. 48 (2009) 6954-6971
9. Klapars A., Antilla J.C., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 123 (2001) 7727-7729
10. Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F. patents Fr 2001 16547 (Fr 2833947-WO0353225).
11. Taillefer, M.; Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Ouali, A. Fr 2002 06717 (Fr2840303-WO03101966).
12. Antilla J.C., Baskin J.M., Barder T.E., and Buchwald S.L. J. Org. Chem. 69 (2004) 5578-5587
13. Altman R.A., and Buchwald S.L. Org. Lett. 8 (2006) 2779-2782
14. Zhu L., Cheng L., Zhang Y., Xie R., and You J. J. Org. Chem. 72 (2007) 2737-2743
15. Sreedhar B., Shiva Kumar K.B., Srinivas P., Balasubrahmanyam V., and Venkanna G.T. J. Mol. Catal. A: Chem. 265 (2007) 183-185
16. Cristau H.-J., Cellier P.P., Spindler J.-F., and Taillefer M. Chem. Eur. J. 10 (2004) 5607-5622
17. Cristau H.-J., Cellier P.P., Spindler J.-F., and Taillefer M. Eur. J. Org. Chem. (2004) 695-709
18. Taillefer M., Xia N., and Ouali A. Angew. Chem., Int. Ed. 46 (2007) 934-936
19. Chan D.M.T., Monaco K.L., Wang R.-P., and Winters M.P. Tetrahedron Lett. 39 (1998) 2933-2936
20. Evans D.A., Katz J.L., and West T.R. Tetrahedron Lett. 39 (1998) 2937-2940
21. Lam P.Y.S., Clark C.G., Saubern S., Adams J., Winters M.P., Chan D.M.T., and Combs A. Tetrahedron Lett. 39 (1998) 2941-2944
22. Ley S.V., and Thomas A.W. Angew. Chem., Int. Ed. 42 (2003) 5400-5449
23. Kantam M.L., Neelima B., Reddy C.V., and Neeraja V. J. Mol. Catal. A: Chem. 249 (2006) 201-206
24. Kantam M.L., Venkanna G.T., Sridhar C., Sreedhar B., and Choudary B.M. J. Org. Chem. 71 (2006) 9522-9524
25. Collman J.P., Zhong M., Zhang C., and Costanzo S. J. Org. Chem. 66 (2001) 7892-7897
26. van Berkel S.S., van den Hoogenband A., Terpstra J.W., Tromp M., van Leeuwen P.W.N.M., and van Strijdonck G.P.F. Tetrahedron Lett. 45 (2004) 7659-7662
27. Nishiura K., Urawa Y., and Soda S. Adv. Synth. Catal. 346 (2004) 1679-1684
28. Reddy K.R., Kumar N.S., Sreedhar B., and Kantam M.L. J. Mol. Catal. A: Chem. 252 (2006) 136-141
29. Collman J.P., Zhong M., Zeng L., and Costanzo S. J. Org. Chem. 66 (2001) 1528-1531
30. Lan J.-B., Chen L., Yu X.-Q., You J.-S., and Xie R.-G. Chem. Commun. (2004) 188-189
31. Darses S., and Genet J.-P. Eur. J. Org. Chem. (2003) 4313-4327
32. Darses S., and Genet J.-P. Chem. Rev. 108 (2007) 288-325
33. Molander G.A., and Ellis N. Acc. Chem. Res. 40 (2007) 275-286
34. Darses S., Genêt J.-P., Brayer J.-L., and Demoute J.-P. Tetrahedron Lett. 38 (1997) 4393-4396
35. Navarre L., Pucheault M., Darses S., and Genet J.-P. Tetrahedron Lett. 46 (2005) 4247-4250
36. Pucheault M., Darses S., and Genet J.-P. Tetrahedron Lett. 43 (2002) 6155-6157
37. Pucheault M., Darses S., and Genet J.-P. J. Am. Chem. Soc. 126 (2004) 15356-15357
38. Pucheault M., Darses S., and Genet J.-P. Chem. Commun. (2005) 4714-4716
39. Pucheault M., Darses S., and Genêt J.-P. Eur. J. Org. Chem. (2002) 3552-3557
40. Pucheault M., Michaut V., Darses S., and Genet J.-P. Tetrahedron Lett. 45 (2004) 4729-4732
41. Genêt J.P., Darses S., and Michelet V. Pure Appl. Chem. 80 (2008) 831-844
42. Quach T.D., and Batey R.A. Org. Lett. 5 (2003) 4397-4400
43. Kabalka G.W., and Zhou L.-L. Lett. Org. Chem. 3 (2006) 320-323
44. 4, filtered, and concentrated under reduced pressure to give the crude N-arylated derivative, which was then purified by flash column chromatography, eluting with heptane/ethyl acetate mixtures, to give the pure N-arylated derivative 2.
45. Amatore C., Cammoun C., and Jutand A. Eur. J. Org. Chem. (2008) 4567-4570
46. Weber M., Singh F.V., Vieira A.S., Stefani H.A., and Paixão M.W. Tetrahedron Lett. 50 (2009) 4324-4327
47. Moreno-Manas M., Perez M., and Pleixats R. J. Org. Chem. 61 (1996) 2346-2351