Suzuki-Miyaura cross-coupling of potassium alkoxyethyltrifluoroborates: Access to aryl/heteroarylethyloxy motifs

Journal of Organic Chemistry

Volumn 77, Issue 22, 2012, Pages 10399-10408

  Fleury Brégeot, Nicolas ^a   Presset, Marc ^b   Beaumard, Floriane ^a   Colombel, Virginie ^b   Oehlrich, Daniel ^b   Rombouts, Frederik ^b   Molander, Gary A ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b Janssen Pharmaceutica   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS-COUPLINGS; INHERENT INSTABILITY; SUZUKI-MIYAURA CROSS-COUPLING;

BROMINE COMPOUNDS; POTASSIUM;

CHEMICAL REACTIONS;

BROMINE DERIVATIVE; POTASSIUM ALKOXYETHYLTRIFLUOROBORATE; POTASSIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; SUZUKI MIYAURA REACTION;

BORATES; CATALYSIS; HETEROCYCLIC COMPOUNDS; MOLECULAR STRUCTURE; OXYGEN; POTASSIUM;

EID: 84869195067     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3021665     Document Type: Article

References (57)

1. Miyaura, N. In Metal-Catalyzed Cross-Coupling Reactions; De Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004; pp 41-123.
2. Miyaura, N. Top. Curr. Chem. 2002, 219, 11
3. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457
4. Seechurn, C. C. C. J.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062
5. Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4544
6. Doucet, H. Eur. J. Org. Chem. 2008, 2013
7. Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417
8. Molander, G. A.; Figueroa, R. Aldrichimica Acta 2005, 38, 49
9. Molander, G. A.; Ellis, N. Acc. Chem. Res. 2007, 40, 275
10. Stefani, H. A.; Cella, R.; Adriano, S. Tetrahedron 2007, 63, 3623
11. Darses, S.; Genet, J.-P. Chem. Rev. 2008, 108, 288
12. Molander, G. A.; Jean-Gérard, L. In Boronic Acids; Hall, D. G., Ed.; Wiley-VCH: Weinheim, 2011; Vol. 2, pp 507-548.
13. Lennox, A. J. J.; Lloyd-Jones, G. C. Isr. J. Chem. 2010, 50, 664
14. Butters, M.; Harvey, J. N.; Jover, J.; Lennox, A. J. J.; Lloyd-Jones, G. C.; Murray, P. M. Angew. Chem., Int. Ed. 2010, 49, 5156
15. Lennox, A. J. J.; Lloyd-Jones, G. C. J. Am. Chem. Soc. 2012, 134, 7431
16. Molander, G. A.; Beaumard, F. Org. Lett. 2011, 13, 3948
17. Colombel, V.; Rombouts, F.; Oehlrich, D.; Molander, G. A. J. Org. Chem. 2012, 77, 2966
18. Fleury-Brégeot, N.; Raushel, J.; Sandrock, D. L.; Dreher, S. D.; Molander, G. A. Chem.-Eur. J. 2012, 18, 9564
19. Molander, G. A.; Beaumard, F. Org. Lett. 2011, 13, 1242
20. Devulapally, R.; Fleury-Brégeot, N.; Molander, G. A.; Seapy, D. G. Tetrahedron Lett. 2012, 53, 1051
21. Molander, G. A.; Fleury-Brégeot, N.; Hiebel, M.-A. Org. Lett. 2011, 13, 1694
22. Molander, G. A.; Shin, I. Org. Lett. 2012, 14, 3138
23. Molander, G. A.; Shin, I. Org. Lett. 2011, 13, 3956
24. Hawthorne, M. F.; Dupont, J. A. J. Am. Chem. Soc. 1958, 80, 5830
25. Matteson, D. S.; Liedtke, J. D. J. Org. Chem. 1963, 28, 1924
26. Matteson, D. S.; Peacock, K. J. Organomet. Chem. 1964, 2, 190
27. Matteson, D. S.; Liedtke, J. D. J. Am. Chem. Soc. 1965, 87, 1526
28. Hawthorne, M. F. J. Am. Chem. Soc. 1961, 83, 2541
29. Pasto, D. J.; Cumbo, C. C. J. Am. Chem. Soc. 1964, 86, 4343
30. Larson, G. L.; Prieto, J. A. Tetrahedron 1983, 39, 855
31. Brown, H. C.; Sharp, R. L. J. Am. Chem. Soc. 1968, 90, 2915
32. Brown, H. C.; Singaram, B. J. Org. Chem. 1984, 49, 945
33. Peterson, P. E.; Stepanian, M. J. Org. Chem. 1988, 53, 1903
34. Tallman, R. C. J. Am. Chem. Soc. 1934, 56, 126
35. Lawrence, J. D.; Takahashi, M.; Bae, C.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 15334
36. Murphy, J. M.; Lawrence, J. D.; Kawamura, K.; Incarvito, C.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 13684
37. Liskey, C. W.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 12422
38. Yang, C.-T.; Zhang, Z.-Q.; Tajuddin, H.; Wu, C.-C.; Liang, J.; Liu, J.-H.; Fu, Y.; Czyzewska, M.; Steel, P. G.; Marder, T. B.; Liu, L. Angew. Chem., Int. Ed. 2012, 51, 528
39. Yi, J.; Liu, J.-H.; Liang, J.; Dai, J.-J.; Yang, C.-T.; Fu, Y.; Liu, L. Adv. Synth. Catal. 2012, 354, 1685
40. Ito, H.; Kubota, K. Org. Lett. 2012, 14, 890
41. Dudnik, A. S.; Fu, G. C. J. Am. Chem. Soc. 2012, 134, 10693
42. Joshi-Pangu, A.; Ma, X.; Diane, M.; Iqbal, S.; Kribs, R. J.; Huang, R.; Wang, C.-Y.; Biscoe, M. R. J. Org. Chem. 2012, 77, 6629
43. The procedure for converting boronic acids and boronate esters to potassium trifluoroborate salts using milder conditions was also tested but did not provide better yields. See: Lennox, A. J. J.; Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2012, 51, 9385
44. Wuts, P. G. M.; Greene, T. W. In Protecting Groups in Organic Synthesis, 3 rd ed.; Greene, T. W.; Wuts, P. G. M., Eds.; John Wiley & Sons, Inc.: Hoboken, NJ, 1999; pp 76-86.
45. Kocienski, P. J. In Protecting Groups, 3 rd ed.; Kocienski, P. J., Ed.; Georg Thieme Verlag: Stuttgart, 2005; pp 241-257.
46. Guram, A. S.; King, A. O.; Allen, J. G.; Wang, X.; Schenkel, L. B.; Chan, J.; Bunel, E. E.; Faul, M. M.; Larsen, R. D.; Martinelli, M. J.; Reider, P. J. Org. Lett. 2006, 8, 1787
47. Colacot, T. J.; Carole, W. A.; Neide, B. A.; Harad, A. Organometallics 2008, 27, 5605
48. He, A.; Falck, J. R. J. Am. Chem. Soc. 2010, 132, 2524
49. Pudasaini, B.; Janesko, B. G. Organometallics 2012, 31, 4610
50. Murai, N.; Yonaga, M.; Tanaka, K. Org. Lett. 2012, 14, 1278
51. Paquette, L. A.; Doherty, A. M.; Rayner, C. M. J. Am. Chem. Soc. 1992, 114, 3910
52. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190
53. Ramanathan, M.; Hou, D.-R. Tetrahedron Lett. 2010, 51, 6143
54. Loire, G.; Prim, D.; Andrioletti, B.; Rose, E.; Persoons, A.; Sioncke, S.; Vaissermann, J. Tetrahedron Lett. 2002, 43, 6541
55. Vechorkin, O.; Proust, V.; Hu, X. J. Am. Chem. Soc. 2009, 131, 9756
56. Mineno, T. Tetrahedron Lett. 2002, 43, 7975
57. Baciocchi, E.; Piermattei, A.; Rol, C.; Ruzziconi, R.; Sebastiani, G. V. Tetrahedron 1989, 45, 7049