Metal catalyst-free by design. the synthesis of amides from alkyl iodides, carbon monoxide and amines by a hybrid radical/ionic reaction

Chemical Communications

Volumn , Issue 18, 1998, Pages 1953-1954

  Ryu, Ilhyong ^a   Nagahara, Kiyoto ^a   Kambe, Nobuaki ^a   Sonoda, Noboru ^a,b   Kreimerman, Sergio ^a   Komatsu, Mitsuo ^a  

^a OSAKA UNIVERSITY   (Japan)

^b KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002629226     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a805815f     Document Type: Article

References (18)

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2. I. T. Horváth and J. Rábai, Science, 1994, 266, 72;
3. J. J. J. Juliette, I. T. Horváth and J. A. Gladysz, Angew. Chem., Int. Ed. Engl., 1997, 36, 1610.
4. Also see a related review: D. P. Curran, Angew. Chem., Int. Ed., 1998, 37, 1174.
5. K. Nasahara, I. Ryu, M. Komatsu and N. Sonoda, J. Am. Chem. Soc., 1997, 119, 5465.
6. 2O (40 ml), filtration, evaporation of filtrate and column chromatography on silica gel gave pure amide 2.
7. -1 at room temp.) of pivaloyl radical are known, see: Y. P. Tsentalovich and H. Fischer, J. Chem. Soc., Perkin Trans. 2, 1994, 729;
8. C. E. Brown, A. G. Neville, D. M. Rayner, K. U. Ingold and L. Lusztyk, Aust. J. Chem., 1995, 48, 363;
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11. P. Renaud, E. Lacôte and L. Quaranta, Tetrahedron Lett., 1998, 39, 2123.
12. Reaction of primary alkyl iodides under thermal initiation conditions suffers from direct aminolysis.
13. For examples of amide synthesis by catalytic carbonylation, see A. Schoenberg and R. F. Heck, J. Org. Chem., 1974, 39, 3327;
14. T. Kobayashi and M. Tanaka, J. Organomet. Chem., 1982, 231, C12;
15. T. Kobayashi and M. Tanaka, J. Organomet. Chem., 1982, 233, C64;
16. F. Ozawa, H. Soyama, T. Yamamoto and A. Yamamoto, Tetrahedron Lett.,1982, 23, 3383;
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18. Also see a related review: A. Yamamoto, Bull. Chem. Soc. Jpn., 1995, 68, 433.