Carbon monoxide free aminocarbonylation of aryl and alkenyl iodides using DMF as an amide source

Organic Letters

Volumn 4, Issue 17, 2002, Pages 2849-2851

  Hosoi, Kazushi ^a   Nozaki, Kyoko ^a,b,c   Hiyama, Tamejiro ^a  

^a KYOTO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000706040     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026236k     Document Type: Article

References (24)

1. Heck, R. F. In Palladium Reagents in Organic Synthesis; Academic Press: London, 1985; p 352.
2. Tsuji, J. In Palladium Reagents and Catalysts; John Wiley and Sons Ltd: Chichester, 1995; p 188.
3. Schoenberg, A.; Heck, R. F. J. Org. Chem. 1974, 39, 3327.
4. Aryl chlorides are also applicable to the amide formation: Perry, R. J.; Wilson, B. D. J. Org. Chem. 1996, 61, 7482.
5. (a) Ozawa, F.; Yamamoto, A. Chem. Lett. 1982, 865.
6. (b) Ozawa, F.; Soyama, H.; Yamamoto, T.; Yamamoto, A. Tetrahedron Lett. 1982, 23, 3383.
7. (c) Ozawa, F.; Soyama, H.; Yanagihara, I.; Aoyama, H.; Takino, K.; Izawa, T.; Yamamoto, T.; Yamamoto, A. J. Am. Chem. Soc. 1985, 107, 3235.
8. (d) Yamamoto, A. Bull. Chem. Soc. Jpn. 1995, 68, 433.
9. Kobayashi, T.; Tanaka, M. J. Organomet. Chem. 1982, 233, C64.
10. Schnyder, A.; Beller, M.; Mehltretter, G. Nsenda, T.; Studer, M.; Indolese, A. F. J. Org. Chem. 2001, 66, 4311.
11. 3 (92.0 mg. 0.60 mmol), and the mixture was heated at 120 °C for 10 h. After aqueous workup, the crude mixture was purified by silica gel column chromatography (hexane/AcOEt = 3/1) to obtain N,N-dimethyl-(4-ethoxycarbonyl)benzamide (2b) in 72% yield.
12. (a) Vilsmeier, A.; Haack, A. Chem. Ber. 1927, 60, 119.
13. (b) James, P. N. In Organic Syntheses; Wiley and Sons: New York, 1963; Collect. Vol. IV, p 539.
14. Examples of oxidative addition of Ar-I to Pd(0): a) Fitton, B. P.; Johnson, M. P.; McKeon, J. E. J. Chem. Soc., Chem. Commun. 1968, 6, See also ref 2.
15. Ishiyama, T.; Hartwig, J. J. Am. Chem. Soc. 2000, 122, 12043.
16. Jun, C.-H.; Hong, J.-B. Org. Lett. 1999, 1, 887.
17. (a) Quan, L. G.; Lamrani, M.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 4827.
18. (b) Quan, L. G.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 3545.
19. (c) Gevorgyan, V.; Quan, L. G.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4089.
20. (a) Tatsumi, T.; Tominaga, H.; Hidai, M.; Uchida, Y. J. Organomet. Chem. 1981, 215, 67.
21. (b) Tsuji, Y.; Yoshii, S.; Ohsumi, T.; Kondo, T.; Watanabe, Y. J. Organomet. Chem. 1987, 331, 379.
22. (a) Meegalla, S. K.; Taylor, N. J.; Rodrigo, R. J. Org. Chem. 1992, 57, 2422.
23. (b) Larock, R. C.; Doty, M. J. J. Org. Chem. 1993, 58, 4579.
24. Satoh, T.; Itaya, T.; Miura, M.; Nomura, M. Chem. Lett. 1996, 823.