Copper-Catalyzed Amidation of Aryl Iodides
J. Chin. Chem. Soc., Vol. 55, No. 3, 2008 653
4. Fagan, P. J.; Hauptman, E.; Shapiro, R.; Casalnuovo, A. J.
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9.0 Hz, 2H).
N-Phenylacetamide (Table 2, entry 7): mp: 113-115
°C; 1H NMR (90 MHz, CDCl3): d 2.1 (s, 3H), 7.0-7.5 (m,
5H), 7.7 (br s, 1H).
5. Beller, M. Angew. Chem. Int. Ed. 1995, 34, 1316.
6. Sturmer, R. Angew. Chem. Int. Ed. 1999, 38, 3307.
7. Sawyer, J. S. Tetrahedron 2000, 56, 5045.
N-(4-Methyl)phenylacetamide (Table 2, entry 9):
mp: 150-152 °C; 1H NMR (500 MHz, CDCl3): d 2.13 (s,
3H), 2.29 (s, 3H), 7.09 (d, J = 8.2 Hz, 2H), 7.34 (br s, 1H),
7.35 (d, J = 8.2 Hz, 2H).
8. Chen, M. Y.; Hsu, J. L.; Shie, J. J.; Fang, J. M. J. Chin.
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Chem. Res. 1998, 31, 853. (c) Yang, B. H.; Buchwald, S. L.
J. Organomet. Chem. 1999, 576, 125.
N-(2-Methyl)phenylacetamide (Table 2, entry 11):
mp: 109-110 °C; 1H NMR (500 MHz, CDCl3): d 2.18 (s,
3H), 2.24 (s, 3H), 6.94 (br s, 1H), 7.06 (t, J = 7.4 Hz, 1H),
7.16-7.20 (m, 2H), 7.74 (d, J = 7.9 Hz, 1H).
11. Lindley, J. Tetrahedron 1984, 40, 1433.
N,N-Diphenylacetamide (Table 2, entry 12): mp:
102-103 °C; 1H NMR (90 MHz, CDCl3): d 2.1 (s, 3H), 7.3-
7.6 (m, 10H).
12. Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002,
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55, 12829. (b) Lipshutz, B. H.; Ueda, H. Angew. Chem. Int.
Ed. Engl. 2000, 39, 4492.
N-(4-Methoxyphenyl)-N-phenylacetamide (Table
2, entry 13): mp: 109-110 °C; 1H NMR (90 MHz, CDCl3): d
2.1 (s, 3H), 3.8 (s, 3H), 6.9 (d, 2H), 7.1-7.6 (m, 7H).
N-(4-Methylphenyl)-N-phenylacetamide (Table 2,
entry 14): mp: 106-108 °C; 1H NMR (90 MHz, CDCl3): d
2.1 (s, 3H), 2.4 (s, 3H), 7.1-7.6 (m, 9H).
14. (a) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem.
Soc. 2002, 124, 7421. (b) Kang, S. K.; Kim, D. H.; Park, J. N.
Synlett, 2002, 427. (c) Crawford, K. R.; Padwa, A. Tetrahe-
dron Lett. 2002, 43, 7365. (d) Deng, W.; Wang, Y. F.; Zou, Y.;
Liu, L.; Guo, Q. X. Tetrahedron Lett. 2004, 45, 2311. (e)
Moriwaki, K.; Satoh, K.; Takada, M.; Ishino, Y.; Ohno, T.
Tetrahedron Lett. 2005, 46, 7559. (f) Jiang, L.; Job, G. E.;
Klapars, A.; Buchwald, S. L. Org. Lett. 2003, 5, 3667. (g)
Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J.
Am. Chem. Soc., 2001, 123, 7727. (h) Chen, Y. J.; Chen, H.
H. Org. Lett. 2006, 8, 5609.
N-(2-Methoxyphenyl)-N-phenylacetamide (Table
2, entry 15): mp: 103-104 °C; 1H NMR (90 MHz, CDCl3): d
2.0 (s, 3H), 3.9 (s, 3H), 6.9 (d, 2H), 7.1-7.6 (m, 7H).
N-(2-Methylphenyl)-N-phenylacetamide (Table 2,
entry 16): mp: 73-74 °C; 1H NMR (90 MHz, CDCl3): d 2.0
(s, 3H), 2.3 (s, 3H), 7.0-7.5 (m, 9H).
15. Blass, B. E. Tetrahedron 2002, 58, 9301.
16. Hosseinzadeh, R.; Tajbakhsh, M.; Mohadjerani, M.; Mehdinejad,
H. Synlett 2004, 9, 1517.
ACKNOWLEDGEMENT
17. Ghaffarinia, A.; Golchoubian, H.; Hosseinzadeh, R. J. Chin.
Chem. Soc. 2005, 52, 531.
Financial support of this work from the Research
Council of Mazandaran University is gratefully acknowl-
edged.
18. (a) Lide, D. R. CRC Handbook of Chemistry and Physics,
79th ed.; CRC Press: Cleveland, 1998. (b) Furniss, B. S.;
Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel’s
Textbook of Practical Organic Chemistry, 5th ed.; Longman:
Harlow, 1989. (c) Buckingham, J.; Macdonald, F. Dictio-
nary of Organic Compounds, 6th ed.; Chapman and Hall:
New York, 1996.
Received November 30, 2007.
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