Environmentally friendly homocoupling reaction of functionalized potassium aryl trifluoroborates salts in aqueous media

Tetrahedron Letters

Volumn 52, Issue 41, 2011, Pages 5288-5291

  Santos Filho, Everaldo F ^a   Sousa, Jokderléa C ^a   Bezerra, Natércia M M ^a   Menezes, Paulo H ^a   Oliveira, Roberta A ^a  

^a FEDERAL UNIVERSITY OF PERNAMBUCO   (Brazil)

Author keywords

Biaryl compounds; Homocoupling reaction; Potassium organotrifluoroborates

Indexed keywords

PALLADIUM; POTASSIUM DERIVATIVE; POTASSIUM TRIFLUOROBORATE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CROSS COUPLING REACTION; DRUG STRUCTURE; FLUORINE NUCLEAR MAGNETIC RESONANCE; HOMOCOUPLING REACTION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 80052583586     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.08.008     Document Type: Article

References (72)

1. P.T. Anastas, and J.C. Warner Green Chemistry: Theory and Practice 2000 Oxford University Press USA
2. I.T. Horvath, and P.T. Anastas Chem. Rev. 107 2007 2169
3. G.J. Hutchings Catal. Today 122 2007 196
4. M. Kidwai Pure Appl. Chem. 78 2006 1983
5. C.-J. Li Chem. Rev. 93 1993 2023
6. C.-J. Li Chem. Rev. 105 2005 3095
7. P.G. Pringle, D. Brewin, M.B. Smith, and K. Worboys I.T. Horvath, F. Joo, Aqueous Organometallic Chemistry and Catalysis 1995 Kluwer Academic Dordrecht
8. P.G. Jessop, and W. Leitner Chemical Synthesis Using Supercritical Fluids 1999 Wiley-VCH Weinheim
9. T. Welton Chem. Rev. 99 1999 2071
10. M.J. Earle, and K.R. Seddon Pure Appl. Chem. 72 2000 1391
11. J.A. Gladysz, D.P. Curran, and I.T. Horvath Handbook of Fluorous Chemistry 2004 Wiley-VCH Weinheim
12. M.C. Kozlowski, B.J. Morgan, and E.C. Linton Chem. Soc. Rev. 38 2009 3193
13. P. Kocovsky, S. Vyskocil, and M. Smrcina Chem. Rev. 103 2003 3213
14. Y. Chen, S. Yekta, and A.K. Yudin Chem. Rev. 103 2003 3155
15. J.M. Brunel Chem. Rev. 105 2005 857
16. G. Casalbore-Miceli, A. DegliEspositi, V. Fattori, G. Marconi, and C. Sabatini Phys. Chem. Chem. Phys. 6 2004 3092
17. A.O. Solak, L.R. Eichorst, W.J. Clark, and R.L. McCreery Anal. Chem. 75 2003 296
18. H.-T. Shih, C.-H. Lin, H.-H. Shih, and C.-H. Cheng Adv. Mater. 14 2002 1409
19. Y.-T. Long, H.-T. Rong, M. Buck, and M. Grunze J. Electroanal. Chem. 524 2002 62
20. A.M. Sarker, L.M. Ding, P.M. Lahti, and F.E. Karasz Macromolecules 35 2002 223
21. S.A. McFarland, and N.S. Finney J. Am. Chem. Soc. 123 2001 1260
22. R. Lemieux Acc. Chem. Res. 34 2001 845
23. H. Schwierz, and F. Vogtle J. Inclusion Phenom. Macro. Chem. 37 2000 309
24. D. Hohnholz, K.H. Schweikart, L.R. Subramanian, A. Wedel, W. Wischert, and M. Hanack Synth. Mater. 110 2000 141
25. V. Percec, A.D. Asandei, and Q. Zheng J. Polym. Sci., Part A: Polym. Chem. 38 2000 3631
26. V. Percec, H. Oda, and A.D. Asandei Chem. Mater. 11 1999 1890
27. I. Cepanec Synthesis of Biaryls 1st ed. 2004 Elsevier Science
28. A. Prastaro, P. Ceci, E. Chiancone, A. Boffi, G. Fabrizi, and S. Cacchi Tetrahedron Lett. 51 2010 2550
29. N. Wu, X.N. Li, X. Xu, Y.M. Wang, Y.Y. Xu, and X. Chen Lett. Org. Chem. 7 2010 11
30. K. Mitsudo, T. Shiraga, and H. Tanaka Tetrahedron Lett. 49 2008 6593
31. Y. Yamamoto Synlett 2007 1913
32. H. Sakurai, H. Tsunoyama, and T. Tsukuda J. Organomet. Chem. 692 2007 368
33. L. Zhou, Q.X. Xu, and H.F. Jiang Chin. Chem. Lett. 18 2007 1043
34. G. Cravotto, G. Palmisano, S. Tollari, G.M. Nano, and A. Penoni Ultrason. Sonochem. 12 2005 91
35. C. Gonzalez-Arellano, A. Corma, M. Iglesias, and F. Sanchez Chem. Commun. 2005 1990
36. S. Carrettin, J. Guzmann, and A. Corma Angew. Chem., Int. Ed. 44 2005 2242
37. S. Punna, D.D. Diaz, and M.G. Finn Synlett 2004 2351
38. H. Tsunoyama, H. Sakurai, N. Ichikuni, Y. Negishi, and T. Tsukuda Langmuir 26 2004 11293
39. L.M. Klingensmith, and N.E. Leadbeater Tetrahedron Lett. 44 2003 765
40. A.S. Demir, O. Reis, and M. Emrullahoglu J. Org. Chem. 68 2003 10130
41. H. Yoshida, Y. Yamaryo, J. Ohshita, and A. Kunai Tetrahedron Lett. 44 2003 1541
42. J.R. Falck, S. Mohapatra, M. Bondlela, and S.K. Venkataraman Tetrahedron Lett. 43 2002 8149
43. G.W. Kabalka, and L. Wang Tetrahedron Lett. 43 2002 3067
44. J.P. Parrish, Y.C. Jung, R.J. Floyd, and K.W. Jung Tetrahedron Lett. 43 2002 7899
45. D.J. Koza, and E. Carita Synthesis 2002 2183
46. M.S. Wong, and X.L. Zhang Tetrahedron Lett. 42 2001 4087
47. K.A. Smith, E.M. Campi, W.R. Jackson, S. Marcuccio, C.G.M. Naeslund, and G.B. Deacon Synlett 1997 131
48. M. Moreno-Manas, M. Perez, and R. Pleixats J. Org. Chem. 61 1996 2346
49. F.A. Grimm, L. Barton, and R.F. Porter Inorg. Chem. 7 1968 1309
50. C.H. Chang, R.F. Porter, and S.H. Bauer Inorg. Chem. 8 1969 1689
51. G.A. Molander, and R. Figueroa Aldrichim. Acta 38 2005 49
52. H.A. Stefani, R. Cella, and A.S. Vieira Tetrahedron 63 2007 3623
53. G.A. Molander, and N. Ellis Acc. Chem. Res. 40 2007 275
54. S. Darses, and J.-P. Genet Chem. Rev. 108 2008 288
55. R.A. Oliveira Synlett 2009 505
56. G.A. Molander, and D.E. Petrillo J. Am. Chem. Soc. 128 2006 9634
57. G.A. Molander, and D.J. Cooper J. Org. Chem. 72 2007 3558
58. G.A. Molander, and R. Figueroa Org. Lett. 8 2006 75
59. B.W. Katona, F. Machrouhi, and G.A. Molander J. Org. Chem. 67 2002 8416
60. G.A. Molander, and R.A. Oliveira Tetrahedron Lett. 49 2008 1266
61. G.A. Molander, and R. Figueroa J. Org. Chem. 71 2006 6135
62. G.A. Molander, J. Ham, and B. Canturk Org. Lett. 9 2007 821
63. R.A. Oliveira, R.O. Silva, G.A. Molander, and P.H. Menezes Magn. Reson. Chem. 47 2009 873
64. R. Smoum, A. Rubinstein, and M. Srebnik Org. Biomol. Chem. 3 2005 941
65. M.-J.R.P. Queiroz, R.C. Calhelha, L.A. Vale-Silva, E. Pinto, R.T. Lima, and M.H. Vasconcelos Eur. J. Med. Chem. 45 2010 5628
66. R.A. Oliveira, L. Savegnago, C.R. Jesse, P.H. Menezes, G.A. Molander, and C.W. Nogueira Basic Clin. Pharmacol. Toxicol. 104 2009 448
67. E. Vedejs, S.C. Fields, R. Hayashi, S.R. Hithccock, D.R. Powell, and M.R. Schrimpf J. Am. Chem. Soc. 121 1999 2460
68. T.E. Barder, S.D. Walker, J.R. Martinelli, and S.L. Buchwald J. Am. Chem. Soc. 127 2005 4685
69. J. Mao, Q. Hua, G. Xie, Z. Yao, and D. Shi Eur. J. Org. Chem. 2009 2262
70. M. Berthod, G. Mignani, G. Woodward, and M. Lemaire Chem. Rev. 105 2005 1801
71. L. Pu Chem. Rev. 98 1998 2405
72. J. Roncali Chem. Rev. 92 1992 711