Browse > Article
http://dx.doi.org/10.5012/bkcs.2013.34.1.42

Functionalization of Organotrifluoroborates via Cu-Catalyzed C-N Coupling Reaction  

Lee, Jung-Hyun (Advanced Organic Synthesis Laboratory, Department of Chemistry and Nano Science, Ewha Womans University)
Kim, Heejin (MarineChemomics Laboratory, Natural Medicine Center, Korea Institute of Science and Technology)
Kim, Taejung (MarineChemomics Laboratory, Natural Medicine Center, Korea Institute of Science and Technology)
Song, Jung Ho (MarineChemomics Laboratory, Natural Medicine Center, Korea Institute of Science and Technology)
Kim, Won-Suk (Advanced Organic Synthesis Laboratory, Department of Chemistry and Nano Science, Ewha Womans University)
Ham, Jungyeob (MarineChemomics Laboratory, Natural Medicine Center, Korea Institute of Science and Technology)
Publication Information
Bulletin of the Korean Chemical Society / v.34, no.1, 2013 , pp. 42-48 More about this Journal
Abstract
Potassium N-heterobiaryltrifluoroborates were successfully prepared via a selective Cu-catalyzed C-N coupling reaction. The $BF_3K$ moiety was well tolerated under the reaction conditions involving CuI and dimethyl-ethylenediamine (DMEDA) in the presence of DMSO. The Pd-catalyzed Suzuki-Miyaura cross couplings of potassium N-heterobiaryltrifluoroborates with bromoarenes were studied to prepare the N-heterotriaryl compounds. Moreover, homocoupling, iodination, and hydroxylation of potassium N-heterobiaryltrifluoroborates provided the corresponding products in high yields.
Keywords
Organotrifluoroborate; Potassium N-heterobiaryltrifluoroborates; Cu-catalyzed C-N coupling; Chan-Lam coupling; N-Heterobiarene;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Talley, J. J.; Penning, T. D.; Collins, P. W.; Rogier, D. J.; Malecha, J. W.; Miyashiro, J. M.; Bertenshaw, S. R.; Khanna, I. K.; Graneto, M. J.; Rogers, R. S.; Carter, J. S.; Docter, S. H.; Yu, S. S. patent WO 95/15316, G. D. Searle & Co., 1995.
2 Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.; Collins, P. W.; Docter, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.; Isakson, P. C. J. Med. Chem. 1997, 40, 1347.   DOI   ScienceOn
3 Mutlib, A. E.; Shockcor, J.; Chen, S. Y.; Espina, R.; Lin, J.; Gracianni, N.; Prakash, S.; Gan L. Drug Metab. Dispos. 2001, 29, 1296.
4 Mutlib, A. E.; Shockcor, J.; Chen, S. Y.; Espina, R.; Pinto, D. J.; Orwatt, M.; Prakash, S.; Gan, L. Chem. Res. Toxicol. 2002, 15, 48.   DOI   ScienceOn
5 Lewis, G. M.; Cassese, R. G.; Heaslip, R. J.; Bansbach, C. C. Agents Action 1993, 39, C89.   DOI
6 Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459.   DOI   ScienceOn
7 Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315.   DOI   ScienceOn
8 Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.   DOI   ScienceOn
9 Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Buchwald, S. L. J. Org. Chem. 2004, 69, 5578.   DOI   ScienceOn
10 Monnier, F.; Taillefer, M. Angew. Chem. Int. Ed. 2009, 48, 6954.   DOI   ScienceOn
11 Kaddouri, H.; Vicente, V.; Ouali, A.; Ouazzani, F.; Taillefer, M. Angew. Chem. Int. Ed. 2009, 48, 333.   DOI   ScienceOn
12 Larsson, P.-F.; Bolm, C.; Norrby, P.-O. Chem. Eur. J. 2010, 16, 13613.   DOI   ScienceOn
13 Senra, J. D.; Aguiar douri, H.; Vicente, V.; Ouali, A.; Ouazzani, F.; Taillefer, M., L. C. S.; Simas, A. B. C. Curr. Org. Synth. 2011, 8, 53.   DOI   ScienceOn
14 Chan, D. M. T.; Monaki, L. L.; Wang, R. P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933.   DOI   ScienceOn
15 Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941.   DOI   ScienceOn
16 Sreedhar, B.; Venkanna, G. T.; Kumar, K. B. S.; Balasubrahmanyamj, V. Synthesis 2008, 5, 795.
17 Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 1381.   DOI   ScienceOn
18 Bolshan, Y.; Batey, R. A. Angew. Chem. Int. Ed. 2008, 47, 2109.   DOI   ScienceOn
19 Qiao, J. X.; Lam, P. Y. S. Synthesis 2011, 6, 829.
20 Rao, K. S.; Wu, T.-S. Tetrahedron 2012, 68, 7735.   DOI
21 Molander, G. A.; Ribagorda, M. J. Am. Chem. Soc. 2003, 125, 11148.   DOI   ScienceOn
22 Molander, G. A.; Petrillo, D. E. J. Am. Chem. Soc. 2006, 128, 9634.   DOI   ScienceOn
23 Molander, G. A.; Ham, J.; Canturk, B. Org. Lett. 2007, 9, 821.   DOI   ScienceOn
24 Molander, G. A.; Ham, J. Org. Lett. 2006, 8, 2767.   DOI   ScienceOn
25 Molander, G. A.; Ellis, N. M. J. Org. Chem. 2006, 71, 7491.   DOI   ScienceOn
26 Molander, G. A.; Cavalcanti, L. N. J. Org. Chem. 2011, 76, 623.   DOI   ScienceOn
27 11. Kabalka, G. W.; Mereddy, A. R. Tetrahedron Lett. 2004, 45, 343.   DOI   ScienceOn
28 Henness, S.; Robinson, D. M.; Lyseng-Williamson, K. A. Drugs 2006, 66, 2109.   DOI   ScienceOn
29 Cho, Y. A.; Kim, D.-S.; Ahn, H. R.; Canturk, B.; Molander, G. A.; Ham, J. Org. Lett. 2009, 11, 4330.   DOI   ScienceOn
30 Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Eur. J. Org. Chem. 2004, 695.
31 McCormack, P. L. Drugs 2011, 71, 2457.   DOI   ScienceOn
32 Kim, D.-S.; Bolla, K.; Lee, S.; Ham, J. Tetrahedron 2011, 67, 1062.   DOI   ScienceOn
33 Ley, S. V.; Thomas, A. W. Angew. Chem. Int. Ed. 2003, 42, 5400.   DOI   ScienceOn
34 Hartwig, J. F. Synlett 2006, 1283.
35 Surry, D. S.; Buchwald, S. L. Angew. Chem. Int. Ed. 2008, 47, 6338.   DOI   ScienceOn
36 Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534.   DOI   ScienceOn
37 Corbet, J. P.; Mignani, G. Chem. Rev. 2006, 106, 2651.   DOI   ScienceOn
38 Elguero, J. Comprehensive Heterocyclic Chemistry, First Edition, Vol. 5; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; p 291.
39 Elguero, J. In Comprehensive Heterocyclic Chemistry II, First Edition, Vol. 3; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon, Elsevier Science Ltd.: Oxford, 1996; p 70.
40 Naito, T.; Yoshikawa, T.; Kitahara, S.; Aoki, N. Chem. Pharm. Bull. 1969, 17, 1467.   DOI
41 Kujubu, D. A.; Fletcher, B. S.; Varnum B. C.; Lim, R. W.; Herschman, H. R. J. Biol. Chem. 1991, 266, 12866.