Palladium-catalyzed synthesis of α-iminoamides from imidoyl chlorides and a carbamoylsilane

Journal of Organic Chemistry

Volumn 70, Issue 13, 2005, Pages 5344-5346

  Cunico, Robert F ^a   Pandey, Rajesh K ^a  

^a NORTHERN ILLINOIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CARBON; CATALYSTS; COMPLEXATION; PALLADIUM; SILANES; SYNTHESIS (CHEMICAL);

Α-IMINOAMIDES; CARBAMOSILANE; IMIDOYL CHLORIDE;

CHLORINE COMPOUNDS;

ALPHA IMINOAMIDE; AMIDE; CARBAMOYLSILANE; CHLORIDE; IMIDOYL CHLORIDE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; DISTILLATION; FILTRATION; HYDROLYSIS; REDUCTION; SUBSTITUTION REACTION; SYNTHESIS;

AMIDES; CATALYSIS; CHLORIDES; IMINES; PALLADIUM; SILANES; STEREOISOMERISM;

EID: 20844448399     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050545h     Document Type: Article

References (26)

1. (a) Chen, J.; Cunico, R. F. Tetrahedron Lett. 2003, 44, 8025-8027.
2. (b) Chen, J.; Cunico, R. F. Tetrahedron Lett. 2002, 43, 8595-8597.
3. (a) Lin, Y.-S.; Alper, H. Angew. Chem., Int. Ed. 2001, 40, 779-781.
4. (b) Detailing, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
5. (a) Masuda, K.; Adachi, J.; Nomura, K. J. Chem. Soc., Perkin 1 1981, 1033-1036.
6. (b) Lopatin, W.; Young, P. R., Jr.; Owen, T. C. J. Am. Chem. Soc. 1979, 101, 960-969.
7. Chen, J.; Cunico, R. F. J. Org. Chem. 2004, 69, 5509-5511.
8. All 3 prepared were monoisomeric and are arbitrarily shown as the Z isomer.
9. (a) Katritzky, A. R.; Hayden, A. E.; Kirichenko, K.; Pelphrey, P.; Ji, Y. J. Org. Chem. 2004, 69, 5108-5111 and references therein.
10. (b) Kantlehner, W.; Mergen, W. W. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Pergamon: Oxford, UK, 1995; Vol. 5, pp 654-660.
11. (c) Kantlehner, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991; Vol. 6, pp 523-529.
12. (d) Sustmann, R.; Korth, H. G. In Methoden der Organische Chemie; Thieme: Stuttgart, Germany, 1985; Vol. E5, pp 628-631.
13. (e) Tennant, G. In Comprehensive Organic Chemistry; Pergamon: Oxford, UK, 1979; pp 469-487.
14. (f) Bonnett, R. In The Chemistry of the Carbon-Nitrogen Bond; Patai, S., Ed.; Interscience: London, UK, 1970; Chapter 13.
15. (g) Ulrich, H. The Chemistry oflmidoyl Halides; Plenum: New York, 1968.
16. (a) Appel, R.; Warning, K.; Ziehn, K.-D. Chem. Ber. 1973, 106, 3450-3454.
17. (b) This method has also been used to form imidoyl chlorides directly from mixtures of carboxylic acids and primary amines: Tamura, K.; Mizukami, H.; Maeda, K.; Watanabe, H.; Uneyama, K. J. Org. Chem. 1993, 58, 32-35.
18. Manley, P. J.; Bilodeau, M. T. Org. Lett. 2002, 4, 3127-3129.
19. The combination of oxalyl chloride and DMF has been used to produce an imidoyl chloride: Zhong, Y.-L.; Lee, J.; Reamer, R. A.; Askin, D. Org. Lett. 2004, 6, 929-931.
20. The same reagents afford amidinium salts (Vilsmeier reagents) from tertiary amides (cf. Bosshard, H. H.; Zollinger, H. Helv. Chim. Acta 1959, 42, 1659-1671).
21. 5 for the preparation of 1 containing R = alkyl on the imide carbon atom did not afford pure imidoyl chlorides.
22. (a) Kobayashi, T.; Sakakura, T.; Tanaka, M. Tetrahedron Lett. 1985, 26, 3463-3466.
23. (b) Tanaka, M.; Kobayashi, T. Synthesis 1985, 967-969.
24. Isolation of similar complexes, prepared by a different route, has been reported: Vicente, J.; Abad, J.-A.; Martinez-Viviente, E.; Jones, P. G. Organometallics 2003, 22, 1967-1978.
25. Cunico, R. F.; Maity, B. C. Org. Lett. 2003, 5, 4947-4949.
26. We do not exclude the possibility that imine to carbene-carbon migration may precede TMSC1 expulsion.