5
58
T. Schareina et al.
LETTER
References and Notes
(18) Stetter, J.; Lieb, F. Angew. Chem. Int. Ed. 2000, 39, 1724;
Angew. Chem. 2000, 112, 1792.
(
1) Grundmann, C. In Houben-Weyl: Methoden der
Organischen Chemie, 4th ed., Vol. E5; Falbe, J., Ed.; Georg
Thieme Verlag: Stuttgart, 1985, 1313–1527.
(
19) (a) Fadda, E.; Chakrabarti, N.; Pomes, R. J. Phys. Chem. B
005, 109, 22629. (b) Syme, C. D.; Nadal, R. C.; Rigby, S.
E. J.; Viles, J. H. J. Biol. Chem. 2004, 279, 18169.
c) Atwood, C. S.; Perry, G.; Zeng, H.; Kato, Y.; Jones, W.
2
(2) Lindley, J. Tetrahedron 1984, 40, 1433.
(
(
3) For a recent catalytic variant of the Sandmeyer reaction, see:
Beletskaya, I. P.; Sigeev, A. S.; Peregudov, A. S.; Petrovskii,
P. V. J. Organomet. Chem.; 2004, 689, 3810.
D.; Ling, K. Q.; Huang, X. D.; Moir, R. D.; Wang, D. D.;
Sayre, L. M.; Smith, M. A.; Chen, S. G.; Bush, A. I.
Biochemistry 2004, 43, 560. (d) Nakamura, M.; Nakajima,
T.; Ohba, Y.; Yamauchi, S.; Lee, B. R.; Ichishima, E.
Biochem. J. 2000, 350, 537. (e) Banci, L.; Bertini, I.; Ciofi-
Baffoni, S.; Katsari, E.; Katsaros, N.; Kubicek, K.; Mangani,
S. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 3994.
20) For the application of 1-alkylimidazoles as solubilizing
additives, see: Welleman, J. A.; Hulsbergen, F. B.; Reedijk, J.
Makromol. Chem. 1981, 182, 785.
21) Initial amination reactions of bromobenzenes in the presence
of Cu/1-butylimidazole showed that these catalysts are also
active for other coupling reactions.
22) All chemicals are commercially available and were used
without further purification. Products were fully
characterized after isolation (NMR, IR, MS, EA) or in the
case of commercially available products by comparison of
GCMS data.
(
4) (a) Hagedorn, F.; Gelbke, H.-P. In Ullmanns Enzyklopädie
der Technischen Chemie, 4th ed., Vol. 17; Bartholomé, E.;
Biekert, E.; Hellmann, H.; Ley, H.; Weigert, W. M.; Weise,
E., Eds.; Verlag Chemie: Weinheim, 1979, 333. (b) Ellis,
G. P.; Romney-Alexander, T. M. Chem. Rev. 1987, 87, 779.
5) Sundermeier, M.; Zapf, A.; Beller, M. Eur. J. Inorg. Chem.
(
(
(
(
(
(
(
(
2003, 3513.
6) Sundermeier, M.; Zapf, A.; Beller, M.; Sans, J. Tetrahedron
Lett. 2001, 42, 6707.
7) Ramnauth, J.; Bhardwaj, N.; Renton, P.; Rakhit, S.;
Maddaford, S. P. Synlett 2003, 2237.
8) Sundermeier, M.; Zapf, A.; Beller, M. Angew. Chem. Int. Ed.
2003, 42, 1661.
9) Sundermeier, M.; Mutyala, S.; Zapf, A.; Spannenberg, A.;
Beller, M. J. Organomet. Chem. 2003, 684, 50.
(
(
10) Chobanian, H. R.; Fors, B. P.; Lin, L. S. Tetrahedron Lett.
006, 47, 3303.
11) Recent examples: (a) Jensen, R. S.; Gajare, A. S.; Toyota,
General Procedure: First, K [Fe(CN) ]·3H O is ground to
4
6
2
2
a fine powder and dried in vacuum (ca. 2 mbar) at 80 °C
overnight. Then, 0.4 mmol dry K [Fe(CN) ], 0.2 mmol
4
6
K.; Yoshifuji, M.; Ozawa, F. Tetrahedron Lett. 2005, 46,
copper precursor, the additive, and 2 mmol aryl halide are
placed in a pressure tube under argon. Afterwards, 200 mL
tetradecane (internal standard for GC) and 2 mL solvent are
added. The pressure tube is sealed and heated for 16 h at the
temperature specified in Table 1 and Table 2. After cooling
to r.t., 3 mL CH Cl are added and the mixture is analyzed
8
645. (b) Veauthier, J. M.; Carlson, C. N.; Collis, G. E.;
Kiplinger, J. L.; John, K. D. Synthesis 2005, 2683.
c) Chidambaram, R. Tetrahedron Lett. 2004, 45, 1441.
12) Schareina, T.; Zapf, A.; Beller, M. Chem. Commun. 2004,
388.
13) Schareina, T.; Zapf, A.; Beller, M. J. Organomet. Chem.
004, 689, 4576.
14) Schareina, T.; Zapf, A.; Beller, M. Tetrahedron Lett. 2005,
6, 2585.
15) (a) Weissman, S. A.; Zewge, D.; Chen, C. J. Org. Chem.
(
(
(
(
(
1
2
2
by GC. Conversion and yield are calculated as an average of
two parallel runs. For isolation of the products the reaction
2
mixture is washed with H O and the organic phase is dried
2
4
over Na SO . After evaporation of the solvents the residue is
2
4
subjected to column chromatography (silica, hexane–
EtOAc). All prepared nitriles are known compounds and
identified by comparison with commercially available
materials.
2
2
005, 70, 1508. (b) Grossman, O.; Gelman, D. Org. Lett.
006, 8, 1189.
(
16) Zanon, J.; Klapars, A.; Buchwald, S. J. Am. Chem. Soc.
003, 125, 2890.
2
1
Analytical data of 5-cyanopyrimidine: H NMR (300
(
17) Cristau, H.-J.; Ouali, A.; Spindler, J.-F.; Taillefer, M. Chem.
Eur. J. 2005, 11, 2483.
MHz, CDCl , 300 K): d = 9.42 (s, 1 H), 9.04 (s, 2 H).
3
13
C NMR (75 MHz, CDCl , 300 K): d = 160.5, 159.5, 114.0,
3
110.2.
Synlett 2007, No. 4, 555–558 © Thieme Stuttgart · New York