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L. Chahen et al.
LETTER
76.62, H 4.71; MS (EI, 70 eV) m/z (%): 204(100) [M+];
(9) (a) Feuerstein, M.; Laurenti, D.; Bougeant, C.; Doucet, H.;
Santelli, M. Chem. Commun. 2001, 325. (b) Feuerstein, M.;
Laurenti, D.; Doucet, H.; Santelli, M. Synthesis 2001, 2320.
(c) Feuerstein, M.; Doucet, H.; Santelli, M. Tetrahedron
Lett. 2001, 42, 5659. (d) Feuerstein, M.; Doucet, H.;
Santelli, M. Tetrahedron Lett. 2001, 42, 6667.
Table 1 (entry 18): d = 7.25–7.10 (m, 3 H, Ph), 7.01 (d, J =
7.2 Hz, 2 H, Ph), 6.89 (s, 2 H, Ar), 4.02 (s, 2 H, CH2), 2.29
(s, 3 H, Me), 2.20 (s, 6 H, Me); Table 1 (entry 25): d = 9.96
(s, 1 H, CHO), 8.14 (d, J = 8.7 Hz, 2 H, Ar), 7.85–7.35 (m,
4 H, Ar), 7.33 (d, J = 8.7 Hz, 2 H, Ar), 4.14 (s, 2 H, CH2);
C14H11NO3 (214.2): calcd. C 69.70, H 4.60; found C 70.01,
H 4.72; MS (EI, 70 eV) m/z (%): 241(100) [M+]; Table 1
(entry 26): d = 8.12 (d, J = 8.7 Hz, 2 H, Ar), 7.34 (d, J = 8.7
Hz, 2 H, Ar), 7.11 (m, 1 H, Ar), 6.82 (m, 2 H, Ar), 4.03 (s, 2
H, CH2); C13H9F2NO2 (249.2): calcd. C 62.65, H 3.64; found
C 62.52, H 3.74; MS (EI, 70 eV) m/z (%): 249(100) [M+];
Table 1 (entry 28): d = 8.08 (d, J = 8.6 Hz, 2 H, Ar), 7.32 (d,
J = 8.6 Hz, 2 H, Ar), 7.25 (m, 1 H, Ar), 7.09 (d, J = 7.3 Hz,
1 H, Ar), 6.89 (m, 2 H, Ar), 4.03 (s, 2 H, CH2), 3.77 (s, 3 H,
Me); Table 1 (entry 35): d = 7.60 (d, J = 7.8 Hz, 2 H, Ar),
7.29 (d, J = 7.8 Hz, 2 H, Ar), 7.10 (d, J = 8.5 Hz, 2 H, Ar),
6.88 (d, J = 8.5 Hz, 2 H, Ar), 4.00 (s, 2 H, CH2), 3.82 (s, 3
H, Me); Table 1 (entry 39): d = 7.53 (d, J = 7.3 Hz, 2 H, Ar),
7.28 (d, J = 7.3 Hz, 2 H, Ar), 7.23 (m, 1 H, Ar), 7.07 (d, J =
7.4 Hz, 1 H, Ar), 6.87 (m, 2 H, Ar), 4.00 (s, 2 H, CH2), 3.78
(s, 3 H, Me); Table 1 (entry 43): d = 7.83 (m, 1 H, Ar), 7.79
(s, 1 H, Ar), 7.67 (d, J = 7.6 Hz, 1 H, Ar), 7.39 (t, J = 7.6 Hz,
1 H, Ar), 7.30 (m, 3 H, Ar), 7.20 (d, J = 7.6 Hz, 1 H, Ar), 4.31
(s, 2 H, CH2), 3.86 (s, 3 H, Me), 2.46 (s, 3 H, Me); C17H16O3
(268.3): calcd. C 76.10, H 6.01; found C 75.87, H 6.21; MS
(EI, 70 eV); m/z (%): 268(36) [M+].
(e) Feuerstein, M.; Doucet, H.; Santelli, M. Synlett 2001,
1458. (f) Feuerstein, M.; Berthiol, F.; Doucet, H.; Santelli,
M. Synlett 2002, 1807. (g) Berthiol, F.; Doucet, H.; Santelli,
M. Eur. J. Org. Chem. 2003, 1091.
(10) As a typical experiment, the reaction of 4-cyanobenzyl
bromide (1.00 g, 5.1 mmol), 4-methoxyphenylboronic acid
(1.55 g, 10.2 mmol) and K2CO3 (1.4 g, 10.2 mmol) at 130 °C
during 20 h in anhydrous xylene (10 mL) in the presence of
cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)
cyclopentane–[PdCl(C3H5)]2 complex (0.0051 mmol) under
argon affords the corresponding adduct after extraction with
ether, evaporation and filtration on silica gel (dichloro-
methane) in 81% (0.92 g) isolated yield. 4-(4-Methoxy-
phenylmethyl)benzonitrile: 1H NMR (300 MHz, CDCl3):
d = 7.59 (d, J = 8.3 Hz, 2 H, Ar), 7.29 (d, J = 8.3 Hz, 2 H,
Ar), 7.11 (d, J = 8.6 Hz, 2 H, Ar), 6.88 (d, J = 8.6 Hz, 2 H,
Ar), 4.00 (s, 2 H, CH2), 3.82 (s, 3 H, OMe).
(11) Analytical data of selected products: Table 1 (entry 11): d =
7.71 (s, 1 H, Ar), 7.62 (s, 2 H, Ar), 7.35–7.10 (m, 5 H, Ph),
4.09 (s, 2 H, CH2); Table 1 (entry 16): d = 7.30–7.00 (m, 5
H, Ph), 7.08 (m, 1 H, Ar), 6.80 (m, 2 H, Ar), 3.94 (s, 2 H,
CH2); C13H10F2 (204.2): calcd. C 76.46, H 4.94; found C
Synlett 2003, No. 11, 1668–1672 © Thieme Stuttgart · New York