S.-H. Kim, R. D. Rieke / Tetrahedron Letters 50 (2009) 5329–5331
5331
Table 4
Supplementary data
Symmetrical and unsymmetrical 2,20-bipyridinesa
Supplementary data (experimental procedure, and copies of 1H,
13C NMR data) associated with this article can be found, in the on-
ZnBr
THF
R
+
N
rt/24h
R
X
N
N
Y
N
X
4a - 4e
1(1.0eq)
(0.8eq)
References and notes
Entry
1
X
Y
I
R
Product
Yieldb (%)
60
1. For recent examples, see: (a) Carey, J. S.; Laffan, D.; Thomson, C.; Wiliams, M. T.
Org. Biomol. Chem. 2006, 4, 2337; (b) Bagley, M. C.; Glover, C.; Merritt, E. A.
Synlett 2007, 2459; (c) Fang, A. G.; Mello, J. V.; Finney, N. S. Org. Lett. 2003, 5, 967.
2. For recent examples, see: (a) Deng, J. Z.; Paone, D. V.; Ginnetti, A. T.; Kurihara,
H.; Dreher, S. D.; Weissman, S. A.; Stauffer, S. R.; Burgey, C. S. Org. Lett. 2009, 11,
345; (b) Yang, D. X.; Colletti, S. L.; Wu, K.; Song, M.; Li, G. Y.; Shen, H. C. Org. Lett.
2009, 11, 381; (c) Voisin-Chiret, A. S.; Bouillon, A.; Burzicki, G.; Celant, M.;
Legay, R.; El-Kashef, H.; Rault, S. Tetrahedron 2009, 65, 607; (d) Hodgson, P. B.;
Salingue, F. H. Tetrahedron Lett. 2004, 45, 685.
3. (a) Schwab, P. F. H.; Fleischer, F.; Michl, J. J. Org. Chem. 2002, 67, 443; (b) Zhang,
N.; Thomas, L.; Wu, B. J. Org. Chem. 2001, 66, 1500; (c) Schubert, U. C.;
Eschbaumer, C.; Heller, M. Org. Lett. 2000, 2, 3373; (d) Gronowitz, S.; Bjork, P.;
Malm, J.; Hornfeldt, A.-B. J. Organomet. Chem. 1993, 460, 127.
4. (a) Sugimoto, O.; Yamada, S.; Tanji, K. J. Org. Chem. 2003, 68, 2054; (b) Song, J. J.;
Yee, N. K.; Tan, Z.; Xu, J.; Kapadia, S. R.; Senanayake, C. H. Org. Lett. 2004, 6,
4905; (c) Duan, X.-F.; Ma, Z.-Q.; Zhang, F.; Zhang, Z.-B. J. Org. Chem. 2009, 74, 939.
5. (a) Savage, S. A.; Smith, A. P.; Fraser, C. L. J. Org. Chem. 1998, 63, 10048; (b) Fang,
Y.-Q.; Hanan, G. S. Synlett 2003, 852; (c) Trecourt, F.; Gervais, B.; Mallet, M.;
Queguiner, G. J. Org. Chem. 1996, 61, 1673; (d) Lutzen, A.; Hapke, M.; Staats, H.;
Bunzen, J. Eur. J. Org. Chem. 2003, 3948.
6. Billingsley, K. L.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 4695.
7. Berman, A. M.; Lewis, J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008,
130, 14926.
H
H
H
H
H
N
N
N
N
4a
Br
2
3
4
I
5-Br
72
65
53
4b
Br
Br
6-Me
6-OMe
N
N
N
4c
Me
N
4d
OMe
8. Li, M.; Hua, R. Tetrahedron Lett. 2009, 50, 1478.
9. Cho, S. H.; Hwang, S. J.; Chang, S. J. Am. Chem. Soc. 2008, 130, 9254.
10. Campeau, L.-C.; Rousseaux, S.; Fagnou, K. J. Am. Chem. Soc. 2005, 127, 18020.
11. Andersson, H.; Almqvist, F.; Olsson, R. Org. Lett. 2007, 9, 1335.
12. Rieke, R. D. Science 1989, 246, 1260.
13. For examples: (a) Rieke, R. D.; Hanson, M. V. Tetrahedron 1997, 53, 1925; (b)
Krasovskiy, A.; Malakhov, V.; Gavryushin, A.; Knochel, P. Angew. Chem., Int. Ed.
2006, 45, 6040.
Me
5
3-Me
I
5-Br
30
Br
N
N
4e
a
Performed with 1 mol %.
Isolated yield (based on electrophile).
14. For a review, see: Kaes, C.; Katz, M.; Hosseini, M. W. Chem. Rev. 2000, 100, 3553.
and see also: 3c references cited therein.
b