Job/Unit: O43624
/KAP1
Date: 02-02-15 14:36:04
Pages: 6
Copper-Catalyzed Synthesis of Imides from Aldehydes or Alcohols
N-Benzoyl-4-bromobenzamide (3f):[ White solid; R
11]
= 0.25 (PE/
f
Acknowledgments
1
AcOEt, 4:1). H NMR (400 MHz, CDCl
3
): δ = 9.23 (s, 1 H), 7.86
(
d, J = 7.3 Hz, 2 H), 7.72 (d, J = 8.5 Hz, 2 H), 7.63–7.58 (m, 3 H),
Financial support from Tongji University (20123231) is gratefully
7
1
1
.49 (t, J = 7.7 Hz, 2 H) ppm. 13C NMR (100 MHz, CDCl
3
): δ = acknowledged.
66.56, 166.43, 133.21, 132.97, 132.14, 131.98, 129.68, 128.82,
28.00 ppm.
[
1] a) M. Klinge, H.-M. Cheng, T. M. Zabriskie, J. C. Vederas, J.
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Jones, H. J. Aust, S. Draeger, B. Shulz, Liebigs Ann. Chem.
N-Benzoyl-2-naphthamide (3g):[
AcOEt, 4:1). H NMR (400 MHz, CDCl
11]
White solid; R
): δ = 9.17 (s, 1 H), 8.38
f
= 0.20 (PE/
1
3
(
s, 1 H), 7.93 (dd, J = 17.0, 8.0 Hz, 6 H), 7.64–7.48 (m, 5 H) ppm.
1
3
3
C NMR (100 MHz, CDCl ): δ = 166.55, 166.52, 135.42, 133.41,
1
1
33.07, 132.40, 130.52, 129.24, 129.08, 128.85, 128.81, 128.56,
28.00, 127.85, 127.11, 123.87 ppm.
1992, 789–798; f) Y. Suhara, H. B. Maruyama, Y. Kotoh, Y.
Miyasaka, K. Yokose, H. Shirai, K. Takano, P. Quitt, P. J.
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N-Benzoylfuran-2-carboxamide (3h):[ White solid; R
11]
= 0.18 (PE/
f
1
AcOEt, 4:1). H NMR (400 MHz, CDCl
d, J = 7.5 Hz, 2 H), 7.62 (d, J = 7.4 Hz, 1 H), 7.58 (s, 1 H), 7.53
t, J = 7.6 Hz, 2 H), 7.40 (d, J = 3.5 Hz, 1 H), 6.63 (dd, J = 3.5,
3
.7 Hz, 1 H) ppm. C NMR (100 MHz, CDCl ): δ = 165.13,
54.88, 146.59, 145.21, 133.35, 133.10, 128.91, 127.76, 118.05,
13.31 ppm.
3
): δ = 9.31 (s, 1 H), 7.90
[
2] a) Z. H. Liu, Q. Q. Ma, Y. X. Liu, Q. M. Wang, Org. Lett.
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2014, 16, 236–239; b) B. M. Trost, K. Hirano, Angew. Chem.
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Int. Ed. 2012, 51, 6480–6483; c) F. Tamaddon, M. R. Sabeti,
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351, 41–45; d) Y. Q. Li, Y. L. Wang, J. Y. Wang, Russ. J. Org.
Chem. 2008, 44, 358–361; e) X. H. Li, Y. Y. Fang, P. C. Deng,
J. C. Hu, T. Li, W. Feng, L. H. Yuan, Org. Lett. 2011, 13, 4628–
1
3
1
1
1
4
631.
[3] a) L. Wang, H. Fu, Y. Y. Jiang, Y. F. Zhao, Chem. Eur. J. 2008,
4, 10722–10726; b) F. Wang, H. X. Liu, H. Fu, Y. Y. Jiang,
4
(
-Chloro-N-(4-methylbenzoyl)benzamide (3j): White solid; R
f
= 0.25
): δ = 9.10 (s, 1 H),
.83–7.73 (m, 4 H), 7.45 (d, J = 8.6 Hz, 2 H), 7.29 (d, J = 8.0 Hz,
H), 2.43 (s, 3 H) ppm. 13C NMR (100 MHz, CDCl
): δ = 166.37,
66.32, 144.17, 139.33, 131.82, 130.11, 129.57, 129.52, 128.97,
28.08, 21.63 ppm. HRMS (ESI): calcd. for C15 12ClNNaO [M
1
PE/AcOEt, 4:1). H NMR (400 MHz, CDCl
3
1
7
2
1
1
Y. F. Zhao, Adv. Synth. Catal. 2009, 351, 246–252; c) J. Wang,
3
C. Liu, J. W. Yuan, A. W. Lei, Chem. Commun. 2014, 50, 4736–
4739.
H
2
[
4] a) W. Wei, Y. Shao, H. Hu, F. Zhang, C. Zhang, Y. Xu, X.
Wan, J. Org. Chem. 2012, 77, 7157–7165; b) E. Shi, Y. Shao, S.
Chen, H. Hu, Z. Liu, J. Zhang, X. Wan, Org. Lett. 2010, 12,
3384–3387; c) L. Ma, X. Wang, W. Yu, B. Han, Chem. Com-
mun. 2011, 47, 11333–11335; d) H. Yu, W. Huang, F. Zhang,
Eur. J. Org. Chem. 2014, 3156–3162; e) H. Yu, F. Zhang, W.
Huang, Synlett 2014, 25, 843–846; f) Z. J. Yang, C. Z. Liu,
B. L. Hu, C. L. Deng, X. G. Zhang, Chem. Commun. 2014, 50,
+
+
Na] 296.0454; found 296.0431.
N-Benzoyl-4-fluorobenzamide (3k):[ White solid; R
3b]
= 0.25 (PE/
f
1
AcOEt, 4:1). H NMR (400 MHz, CDCl
3
): δ = 9.13 (s, 1 H), 7.93–
7
7
1
1
.83 (m, 4 H), 7.60 (t, J = 7.4 Hz, 1 H), 7.49 (t, J = 7.7 Hz, 2 H),
.16 (t, J = 7.6 Hz, 2 H) ppm. 1 C NMR (100 MHz, CDCl
3
3
): δ =
66.56, 165.93, 133.13, 130.81, 130.72, 128.82, 127.96, 116.02,
15.80 ppm.
1
4554–14557; g) J. Zhang, Y. Shao, H. Wang, Q. Luo, J. Chen,
D. Xu, X. Wan, Org. Lett. 2014, 16, 3312–3315.
[
5] a) W. J. Yoo, C. J. Li, J. Am. Chem. Soc. 2006, 128, 13064–
N-Benzoyl-N-methylbenzamide (3n):[ White solid; R
8]
= 0.60 (PE/
f
13065; b) S. C. Ghosh, J. S. Ngiam, C. L. Chai, A. M. Seayad,
1
AcOEt, 4:1). H NMR (400 MHz, CDCl
H), 7.30 (t, J = 7.4 Hz, 2 H), 7.21 (t, J = 7.5 Hz, 4 H), 3.52 (s, 3
3
): δ = 7.47 (d, J = 7.2 Hz,
T. T. Dang, A. Q. Chen, Adv. Synth. Catal. 2012, 354, 1407–
1412; c) S. C. Ghosh, J. S. Y. Ngiam, A. M. Seayad, T. T. Dang,
C. L. L. Chai, A. Q. Chen, J. Org. Chem. 2012, 77, 8007–8015.
4
13
H) ppm. C NMR (100 MHz, CDCl
28.75, 128.25, 34.23 ppm.
3
): δ = 174.37, 136.01, 131.80,
1
[6] A. A. Taherpour, A. Abramian, H. Kardanyazd, Youji Huaxue
007, 27, 123–125.
2
Ethyl 2-Benzamidoacetate (4):[
5a]
[7] X. Y. Yan, K. Fang, H. L. Liu, C. J. Xi, Chem. Commun. 2013,
White solid; R
AcOEt, 4:1). H NMR (400 MHz, CDCl ): δ = 7.82 (d, J = 7.1 Hz,
H), 7.51 (t, J = 7.4 Hz, 1 H), 7.43 (t, J = 7.4 Hz, 2 H), 6.85 (s, 1
H), 4.31–4.18 (m, 4 H), 1.31 (t, J = 7.1 Hz, 3 H) ppm. C NMR
100 MHz, CDCl ): δ = 170.04, 167.42, 133.67, 131.69, 128.52,
27.01, 61.56, 41.81, 14.08 ppm.
f
= 0.45 (PE/
1
49, 10650–10652.
8] H. Yu, J. Shen, Org. Lett. 2014, 16, 3204–3207.
3
[
[
[
2
9] H. E. De La Mare, J. Org. Chem. 1960, 25, 2114–2116.
10] L. Xu, S. H. Zhang, M. L. Trudell, Chem. Commun. 2004,
13
(
3
1668–1669.
1
[
11] L. F. Ran, Z. H. Ren, Y. Y. Wang, Z. H. Guan, Chem. Asian J.
2014, 9, 577–583.
Supporting Information (see footnote on the first page of this arti-
cle): Copies of the H and C NMR spectra.
Received: December 13, 2014
1
13
Published Online:
Eur. J. Org. Chem. 0000, 0–0
© 0000 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
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