A. M. Zawisza, J. Muzart / Tetrahedron Letters 48 (2007) 6738–6742
6741
127.9
100
90
80
70
60
50
40
30
20
10
0
129.1
64.3
102.0
125.9
51.2 63.1
52.1
75.1
130.2
131.2
73.9 77.1
87.0
101.0 103.1
62.1
79.1 86.0
104.1
97.9
50
60
70
80
90
100
m/z
110
120
130
140
150
Graph 2. Mass spectrum of the reduced compound obtained from 2-bromonaphthalene in DMF-d7.
2001, 42, 2301–2303; (c) Viciu, M. S.; Grasa, G. A.;
Nolan, S. P. Organometallics 2001, 20, 3607–3612; (d)
Faucher, N.; Ambroise, Y.; Cintrat, J.-C.; Doris, E.;
Pillon, F.; Rousseau, B. J. Org. Chem. 2002, 67, 932–934;
(e) Sajiki, H.; Kume, A.; Hattori, K.; Hirota, K. Tetra-
hedron Lett. 2002, 43, 7247–7250; (f) Rahaim, R. J., Jr.;
Maleczka, R. E., Jr. Tetrahedron Lett. 2002, 43, 8823–
8826; (g) Cellier, P. P.; Spindler, J.-F.; Taillefer, M.;
Cristau, H.-J. Tetrahedron Lett. 2003, 44, 7191–7195; (h)
Arcadi, A.; Cerichelli, G.; Chiarini, M.; Vico, R.; Zorzan,
D. Eur J. Org. Chem. 2004, 3404–3407; (i) Navarro, O.;
Kaur, H.; Mahjoor, P.; Nolan, S. P. J. Org. Chem. 2004,
69, 3173–3180; (j) Chae, J.; Buchwald, S. L. J. Org. Chem.
2004, 69, 3336–3339; (k) Bei, X.; Hagemeyer, A.; Volpe,
A.; Saxton, R.; Turner, H.; Guram, A. S. J. Org. Chem.
2004, 69, 8626–8633; (l) Monguchi, Y.; Kume, A.; Hattori,
K.; Maegawa, T.; Sajiki, H. Tetrahedron 2006, 62, 7926–
7933; (m) Chen, J.; Zhang, Y.; Yang, L.; Zhang, X.; Liu,
J.; Li, L.; Zhang, H. Tetrahedron 2007, 63, 4266–4270.
9. KF/Al2O3 prepared as previously described: Ferroud, D.;
Geneˆt, J.-P.; Muzart, J. Tetrahedron Lett. 1984, 25, 4379–
4382.
could, in some cases, explain the increase in the perfor-
mance of Pd-catalyzed reductions when they are carried
out in DMF.19
Acknowledgment
We are grateful to CNRS for a temporary position to
A.M.Z.
References and notes
´
1. Ganchegui. B.; Zawisza, A. M.; Gonzalez, I.; Bouquillon,
´
S.; Roglans, A.; Henin, F.; Muzart, J., to be published.
2. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R.
Purification of Laboratory Chemicals; Pergamon: Oxford,
1966, p 143.
3. (a) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew.
Chem., Int. Ed. Engl. 1995, 34, 1348–1350; (b) Marcoux,
J.-F.; Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1997, 62,
1568–1569; (c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem.
2000, 65, 1144–1157.
4. (a) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996,
118, 7217–7218; (b) Kataoka, N.; Shelby, Q.; Stambuli, J.
P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553–
5566.
10. We did not try to determine the yields of the biaryl
compounds since (i) this reaction pathway was out of the
scope of the present study and (ii) various methods are
available for their synthesis.11 Subsequent experiments
have shown that these yields are highly dependent on the
nature of the halogen of the starting aryl halide, the ligand
and the solvent.
´
11. For a review, see: Hassan, J.; Sevignon, M.; Gozzi, C.;
5. Brenda, M.; Knebelkamp, A.; Greiner, A.; Heitz, W.
Synlett 1991, 809–810.
Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359–1470.
12. Murahashi, S.-I.; Yoshimura, N.; Tsumiyama, T.; Koj-
ima, T. J. Am. Chem. Soc. 1983, 105, 5002–5011.
`
6. Legros, J.-Y.; Primault, G.; Toffano, M.; Riviere, M.-A.;
Fiaud, J.-C. Org. Lett. 2000, 4, 433–436.
13. Hartwig, J. F.; Richards, S.; Baranano, D.; Paul, F. J. Am.
7. For a review of reduction methods of aryl halides, see:
March, J. Advanced Organic Chemistry, 4th ed.; Wiley:
New York, 1992, pp 566–567.
8. For recent references concerning the reduction methods of
aryl halides, see: (a) Villemin, D.; Nechab, B. J. Chem.
Res. (S) 2000, 432–434; (b) Angeloff, A.; Brunet, J.-J.;
Legars, P.; Neibecker, D.; Souyri, D. Tetrahedron Lett.
˜
Chem. Soc. 1996, 118, 3626–3633.
14. We have not been able to determine the amount of
deuterium incorporation.
15. (a) Rusina, A.; Vlcˇek, A. A. Nature 1965, 205, 295–296; (b)
Serp, P.; Hernandez, M.; Richard, B.; Kalck, P. Eur. J.
Inorg. Chem. 2001, 2327–2336.