General and highly efficient fluorinated-N-heterocyclic carbene-based catalysts for the palladium-catalyzed Suzuki-Miyaura reaction

Tetrahedron

Volumn 68, Issue 32, 2012, Pages 6535-6547

  Liu, Taoping ^a   Zhao, Xiaoming ^a   Shen, Qilong ^a   Lu, Long ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Aryl halides; Fluoride; Heteroaryl halides; N Heterocyclic carbene; Suzuki Miyaura reaction

Indexed keywords

BORONIC ACID DERIVATIVE; CARBENE; CHLORIDE; HALIDE; IMIDAZOLE DERIVATIVE; PALLADIUM; WATER;

ARTICLE; CATALYST; DEPROTECTION REACTION; FLUORINATION; HYDROGENATION; PRIORITY JOURNAL; ROOM TEMPERATURE; SUZUKI REACTION; TEMPERATURE;

EID: 84862771222     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.05.068     Document Type: Article

References (61)

1. N. Miyaura, K. Yamada, and A. Suzuki Tetrahedron Lett. 36 1979 3437
2. F. Bellina, A. Carpita, and R. Rossi Synthesis 15 2004 2419
3. N. Miyaura Chapter 2 F. Diederich, A. de Meijere, Metal-catalyzed Cross-coupling Reaction 2004 Wiley-VCH New York, NY
4. N. Miyaura Top. Curr. Chem. 219 2002 11
5. A.F. Littke, and G.C. Fu Angew. Chem., Int. Ed. 41 2002 4176
6. R. Martin, and S.L. Buchwald Acc. Chem. Res. 41 2008 1461
7. R.A. Altman, and S.L. Buchwald Nature Protocols 2 2007 3115
8. M.R. Netherton, C. Dai, K. Neuschuta, and G.C. Fu J. Am. Chem. Soc. 123 2001 10099
9. J.H. Kirchoff, M.R. Netherton, I.D. Hills, and G.C. Fu J. Am. Chem. Soc. 124 2002 13662
10. W.A. Herrmann, C.P. Reisinger, and M. Spiegler J. Organomet. Chem. 557 1998 93
11. W.A. Herrmann Angew. Chem., Int. Ed. 41 2002 1290
12. N. Marion, O. Navarro, J. Mei, E.D. Stevens, N.M. Scott, and S.P. Nolan J. Am. Chem. Soc. 128 2006 4101
13. O. Navarro, N. Marion, J. Mei, and S.P. Nolan Chem. - Eur. J. 12 2006 5142
14. M.G. Organ, S.C. Alimsiz, M. Sayah, K.H. Hoi, and A.J. Lough Angew. Chem., Int. Ed. 48 2009 2383
15. G. Altenhoff, R. Goddard, C.W. Lehmann, and F. Glorius J. Am. Chem. Soc. 126 2004 15195
16. A. Zapf, A. Ehrentraut, and M. Beller Angew. Chem., Int. Ed. 39 2000 4153
17. A. Zapf, R. Jackstell, F. Rataboul, T. Riermeier, A. Monsees, C. Fuhrmann, N. Shaikh, U. Dingerdissen, and M. Beller Chem. Commun. 2004 38
18. A. Fihri, D. Luart, C. Len, A. Solhy, and C.P.V. Chevrinb Dalton Trans. 40 2011 3116
19. J.-C. Hierso, A. Fihri, R. Amardeil, P. Meunier, H. Doucet, and M. Santelli Tetrahedron 61 2005 9759
20. A. Scivanti, V. Beghetto, U. Matteoli, S. Antonaroli, A. Marini, and B. Crociani Tetrahedron 61 2005 9752
21. W.-M. Dai, Y. Li, Y. Zhang, K.W. Lai, and J. Wu Tetrahedron Lett. 45 2004 1999
22. M. Joshaghani, M. Daryanavard, E. Rafiee, J. Xiao, and C. Collin Baillie Tetrahedron Lett. 48 2007 2025
23. R. Arvela, N.E. Leadbeater, T.L. Mack, and C.M. Kormos Tetrahedron Lett. 47 2006 217
24. N. Jiang, and A.J. Ragauskas Tetrahedron Lett. 47 2006 197
25. D.-H. Lee, and M.-J. Jin Org. Lett. 13 2011 252
26. J.-C. Hierso, M. Beaupérin, and P. Meunier Eur. J. Inorg. Chem. 2007 3767
27. O. Diebolt, P. Braunstein, S.P. Nolan, and C.S.J. Cazin Chem. Commun. 2008 3190
28. C. Baillie, L. Zhang, and J. Xiao J. Org. Chem. 69 2004 7779
29. F.Y. Kwong, W.H. Lam, C.H. Yeung, K.S. Chan, and A.S.C. Chan Chem. Commun. 2004 1922
30. J.W. Sprengers, J. Wassenaar, N.D. Clement, K.G. Cavell, and C.J. Elsevier Angew. Chem., Int. Ed. 44 2005 2026
31. R. Jackstell, M. Gómez Andreu, A. Frisch, K. Selvakumar, A. Zapf, H. Klein, A. Spannenberg, D. Röttger, O. Briel, R. Karch, and M. Beller Angew. Chem., Int. Ed. 41 2002 986
32. E.A.B. Kantchev, C.J. O'Brien, and M.G. Organ Angew. Chem., Int. Ed. 46 2007 2768
33. C. Valente, S. Çalimsiz, K.H. Hoi, D. Mallik, M. Sayah, and M.G. Organ Angew. Chem., Int. Ed. 51 2012 3314
34. A.J. Arduengo III, R.L. Harlow, and M. Kline J. Am. Chem. Soc. 113 1991 361
35. A.J. Arduengo III Acc. Chem. Res. 32 1999 913
36. D. Bourissou, O. Guerret, F.P. Gabba, and G. Bertrand Chem. Rev. 100 2000 39
37. W.A. Herrmann, and C. Kacher Angew. Chem., Int. Ed. 36 1997 2162
38. J.A. Joule, and K. Mills Heterocyclic Chemistry 2000 Blackwell Science Malden, MA
39. E. Tyrell, and P. Brookes Synthesis 4 2004 469
40. K.L. Billingsley, K.W. Anderson, and S.L. Buchwald Angew. Chem., Int. Ed. 45 2006 3484
41. K. Billingsley, and S.L. Buchwald J. Am. Chem. Soc. 129 2007 3358
42. T.E. Barder, and S.L. Buchwald Org. Lett. 6 2004 2649
43. I. Kondolff, H. Doucet, and M. Santelli Synlett 2005 2057
44. A.E. Thompson, G. Hughes, A.S. Batsanov, M.R. Bryce, P.R. Parry, and B. Tarbit J. Org. Chem. 70 2005 388
45. N. Kudo, M. Pereghini, and G.C. Fu Angew. Chem., Int. Ed. 45 2006 1282
46. A.S. Guram, A.O. King, J.G. Allen, X. Wang, L.B. Schenkel, J. Chan, E.E. Bunel, M.M. Faul, R.D. Larsen, M.J. Martinelli, and P.J. Reider Org. Lett. 8 2006 1787
47. C.E. Garret, and K. Prasad Adv. Synth. Catal. 346 2004 889
48. Y.M.A. Yamada, T. Watanabe, T. Beppu, N., Fukuyama, K. Torri, and Y. Uozumi Chem. - Eur. J. 16 2010 11311
49. L. Ackermann, and A. Althammer Org. Lett. 8 2006 3457
50. I. Kondolff, H. Doucet, and M. Santelli J. Heterocycl. Chem. 45 2008 109
51. N.M. Chaignon, I.J.S. Fairlamb, A.R. Kapdi, R.J.K. Taylor, and A.C. Whitwood J. Mol. Catal. A 219 2004 191
52. C.A. Fleckenstein, and H. Plenio Chem. - Eur. J. 14 2008 4267
53. M.B. Andrus, and C. Song Org. Lett. 3 2001 3761
54. D.-H. Lee, M. Choi, B.-W. Yu, R. Ryoo, A. Taher, S. Hossain, and M.-J. Jin Adv. Synth. Catal. 351 2009 2912
55. G. Saini, N.T. Lucas, and J. Jacob Tetrahedron Lett. 51 2010 2956
56. M.A. Pena, J.P. Sestelo, and L.A. Sarandeses J. Org. Chem. 72 2007 1271
57. J.J.D. de Jong, L.N. Lucas, R. Hania, A. Pugzlys, R.M. Kellogg, B.L. Feringa, K. Duppen, and J.H. van Esch Eur. J. Org. Chem. 10 2003 1887
58. B. Sreedhar, D. Yada, and P.S. Reddy Adv. Synth. Catal. 343 2011 2823
59. M. Lourak, R. Vanderesse, Y. Fort, and P. Caubere J. Org. Chem. 54 1989 4844
60. X. Han, Z. Weng, and T.S.A. Hor J. Organomet. Chem. 692 2007 5690
61. J. Mao, J. Guo, F. Fang, and S.-J. Ji Tetrahedron 64 2008 3905