FranÅois-Xavier Felpin et al.
FULL PAPERS
(
20% AcOEt:petroleum ether) gave a white solid; mp 878C Acknowledgements
[28]
À1
1
[Lit. 908C]. IR (KBr): n=1641, 1716, 2964 cm ; H NMR
(
1
CDCl , 250 MHz): d=3.79 (s, 3H), 3.83 (s, 3H), 6.31 (d,
This work was supported by the “Universitꢀ de Bordeaux”
and the “Centre National de la Recherche Scientifique
(CNRS).” Evonik Degussa GmbH, Buisess Line Catalysts
are gratefully acknowledged for the gift of Pd/C catalysts. We
thank M. Olivier Brugier (Universitꢀ de Montpellier) for
ICP-MS analyses. We also aknowledge Mrs Odile Babot,
Mrs Marie-Hꢀlꢁne Lescure, Mrs Isabelle Ly and Mrs Marion
Zanese (Universitꢀ de Bordeaux) for technical assistance.
3
H, J=15.9 Hz), 6.90 (dm, 2H, J=8.8 Hz), 7.47 (dm, 1H,
13
J=8.8 Hz), 7.65 (d, 1H, J=15.9 Hz); C NMR (CDCl3,
7
1
(
5 MHz): d=51.8, 52.2, 120.1, 127.9, 130.0, 131.3, 138.5,
43.4, 166.4, 166.9; MS (EI): m/z=192 (M), 161
MÀOCH ).
3
(
E)-Methyl 2,4,6-trimethylcinnamate (11): This compound
was prepared according to the general procedure, with di-
azonium salt (1 mmol), acrylate (2 mmol), CaCO3
(
0.5 mmol) and 5% Pd(II)/Ceggshell (1 mol%) in MeOH
(
2.5 mL) at 458C. Purification by flash chromatography (5%
References
AcOEt:petroleum ether) gave a white solid; mp 508C. IR
(
2
À1
1
KBr): n=1637, 1718, 2960, 2949 cm ; H NMR (CDCl3,
50 MHz): d=2.29 (s, 3H), 2.33 (s, 3H), 3.82 (s, 3H), 6.07
d, 1H, J=16.5 Hz), 6.90 (s, 2H), 7.86 (d, 1H, J=16.5 Hz);
[
1] For selected reviews, see: a) V. Farina, Adv. Synth.
Catal. 2004, 346, 1553–1582; b) H.-U. Blaser, A. Indo-
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Chem. Commun. 2005, 431–440; d) K. C. Nicolaou,
P. G. Bulger, D. Sarlah, Angew. Chem. Int. Ed. 2005, 44,
(
13
C NMR (CDCl , 75 MHz): d=21.0, 21.0, 51.6, 122.8, 129.1,
3
1
30.9, 136.8, 138.3, 143.4, 167.4; MS (EI): m/z=204 (M), 189
(
2
MÀCH ), 173 (MÀ2CH ); HR-MS (electrospray): m/z=
3
3
+
27.1041, calcd. for C H O Na (M+Na ): 227.1042.
13 16 2
4
1
442–4489; e) G. Zeni, R. C. Larock, Chem. Rev. 2006,
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(
E)-Ethyl 4-nitrocinnamate (12): This compound was pre-
pared according to the general procedure, with diazonium
salt (1.2 mmol), acrylate (1 mmol), CaCO (0.6 mmol) and
C. W. Jones, Adv. Synth. Catal. 2006, 348, 609–679.
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3
[
[
5
% Pd(II)/Ceggshell (0.1 mol%) in MeOH (2.5 mL) at 258C.
Purification by flash chromatography (70%
CH Cl :petroleum ether) gave a white solid; mp 138–1398C
1
971, 44, 581–582.
3] R. F. Heck, J. P. NolleyJr. , J. Org. Chem. 1972, 37,
2
2
5g]
[
2320–2322.
[Lit. 138.5–1398C]. IR (KBr): n=1645, 1713, 2938, 2984,
À1
1
[4] For a review on diazonium salts, see: A. Roglans, A.
3
7
7
1
1
2
080 cm ; H NMR (CDCl , 250 MHz): d=1.35 (t, 3H, J=
3
Pla-Quintana, M. Moreno-MaÇas, Chem. Rev. 2006,
.0 Hz), 4.29 (q, 2H, J=7.3 Hz), 6.55 (d, 1H, J=16.1 Hz),
.67 (d, 2H, J=8.8 Hz), 7.70 (d, 1H, J=15.9 Hz), 8.24 (d,
1
06, 4622–4643.
13
[5] For representative examples, see: a) K. Kikukawa, K.
Maemura, Y. Kiseki, F. Wada, T. Matsuda, J. Org.
Chem. 1981, 46, 4885–4888; b) D. F. Oliveira, E. A. Se-
verino, C. R. D. Correia, Tetrahedron Lett. 1999, 40,
H, J=8.8 Hz); C NMR (CDCl , 50 MHz): d=14.2, 61.0,
3
22.5, 124.1, 128.6, 140.5, 141.6, 148.4, 166.0; MS (EI): m/z
21 (M), 176 (MÀOC H ).
2
5
(
E)-t-Butyl 4-nitrocinnamate (13): This compound was
2
083–2086; c) E. A. Severino, E. R. Costenaro, A. L. L.
prepared according to the general procedure, with diazoni-
Garcia, C. R. D. Correia, Org. Lett. 2003, 5, 305–308;
d) B. Schmidt, Chem. Commun. 2003, 1656–1657;
e) A. C. B. Burtoloso, A. L. L. Garcia, K. C. Miranda,
C. R. D. Correia, Synlett 2006, 3145–3149; f) R. Perez,
D. Veronese, F. Coelho, O. A. C. Antunes, Tetrahedron
Lett. 2006, 47, 1325–1328; g) E. Artuso, M. Barbero, I.
Degani, S. Dughera, R. Fochi, Tetrahedron 2006, 62,
3146–3157; h) P. R. R. Meira, A. V. Moro, C. R. D.
Correia, Synthesis 2007, 2279–2286.
um salt (1.2 mmol), acrylate (1 mmol), CaCO (0.6 mmol)
and 5% Pd(II)/Ceggshell (0.1 mol%) in MeOH (2.5 mL) at
3
2
58C. Purification by flash chromatography (10% AcOEt:
[29]
petroleum ether) gave a white solid; mp 1498C [Lit. 146–
À1
1
478C]. IR (KBr): n=1639, 1709, 2941, 2982, 3077 cm ;
1
H NMR (CDCl , 250 MHz): d=1.54 (s, 3H), 6.49 (d, 1H,
3
J=15.8 Hz), 7.60 (d, 1H, J=15.2 Hz), 7.65 (d, 1H, J=
1
3
8
7
1
.5 Hz), 8.23 (d, 1H, J=8.8 Hz);
C NMR (CDCl3,
5 MHz): d=28.1, 124.1, 124.6, 128.5, 140.5, 140.9, 148.3,
65.2; MS (EI): m/z=249 (M), 176 (MÀOC H ).
[
[
6] a) M. Beller, K. Kꢂhlein, Synlett 1995, 441–442; b) H.
Brunner, N. Le Cousturier de Courcy, J.-P. GenÞt, Tet-
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Le Cousturier de Courcy, J.-P. GenÞt, Synlett 2000, 201–
4
9
(
E)-N,N-Dimethyl-3-(4-nitrophenyl)acrylamide (14): This
compound was prepared according to the general procedure,
with diazonium salt (1.2 mmol), acrylate (1 mmol), CaCO3
2
04.
(
0.6 mmol) and 5% Pd(II)/Ceggshell (0.5 mol%) in MeOH
7] L. Yin, J. Liebscher, Chem. Rev. 2007, 107, 133–173.
(
2.5 mL) at 458C. Purification by flash chromatography (4%
[30]
[8] a) F.-X. Felpin, T. Ayad, S. Mitra, Eur. J. Org. Chem.
2006, 2679–2690; b) M. Seki, Synthesis 2006, 2975–
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6441–6446; b) F.-X. Felpin, J. Org. Chem. 2005, 70,
MeOH:CH Cl ) gave a white solid; mp 174–1758C [Lit.
2
2
À1
1
76–1788C]. IR (KBr): n=1614, 1654, 2932, 3060 cm ;
1
H NMR (CDCl , 200 MHz): d=3.09 (s, 3H), 3.20 (s, 3H),
3
[
7
.02 (d, 1H, J=15.4 Hz), 7.66 (d, 1H, J=8.6 Hz), 7.69 (d,
H, J=15.9 Hz), 8.23 (d, 1H, J=8.9 Hz); C NMR (CDCl3,
0 MHz): d=36.0, 37.4, 121.7, 124.1, 128.3, 139.5, 141.6,
13
1
5
1
8
575–8578; c) F.-X. Felpin, C. Lory, H. Sow, S. Acher-
ar, Tetrahedron 2007, 63, 3010–3016; d) R. H. Taylor,
F.-X. Felpin, Org. Lett. 2007, 9, 2911–2914; e) F.-X.
Felpin, E. Fouquet, Adv. Synth. Catal. 2008, 350, 863–
48.0, 165.6; MS (EI): m/z=220 (M), 176 [MÀN
ACHTUNGTNRENUNG( CH ) ].
3 2
8
68.
[
10] K. Kçhler, R. G. Heidenreich, J. G. E. Krauter, J.
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2564
ꢁ 2008 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2008, 350, 2559 – 2565