Catalytic and regioselective synthesis of gem- or trans-α,β -unsaturated amides by carbonylation of alkyl alkynes with aniline derivatives by palladium(II) and phosphine

Applied Organometallic Chemistry

Volumn 17, Issue 12, 2003, Pages 921-931

  El Ali, Bassam ^a   Tijani, Jimoh ^a  

^a KING FAHD UNIVERSITY OF PETROLEUM AND MINERALS   (Saudi Arabia)

Author keywords

Alkynes; Aniline; Carbonylative addition; Dppb; Palladium; Syngas; Unsaturated amides

Indexed keywords

1,3 BIS(DIPHENYLPHOSPHINO)PROPANE; 1,4 BIS(DIPHENYLPHOSPHINO)BUTANE; ALKYNE; ALPHA,BETA UNSATURATED AMIDE; AMINE; ANILINE DERIVATIVE; CARBONYL DERIVATIVE; METHYL CHLORIDE; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; SOLVENT; TOLUENESULFONAMIDE DERIVATIVE; TOLUENESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0345600241     PISSN: 02682605     EISSN: None     Source Type: Journal    
DOI: 10.1002/aoc.548     Document Type: Article

References (31)

1. Zabicky J. The Chemistry of Amides. Interscience-Wiley: New York, 1970.
2. Myagchenkov SM, Kurenkov VF. Polym. Plast. Technol. Eng. 1991; 30: 109.
3. Colquhoun HM, Thompson DJ, Twigg MV. Carbonylation: Direct Synthesis of Carbonyl Compound. Plenum Press: New York, 1991.
4. El Ali B, Alper H. In Hydrocarboxylation and Hydroesterification Reactions Catalyzed by Transition Metal Complexes, Beller M, Bolm C (eds). Wiley: New York, 1998; 47.
5. Yamada SI, Shioiri T. Tetrahedron Lett. 1973; 18: 1595.
6. Shiohara K, Okumoto H. Polym. J. 1998; 30: 249.
7. Reppe W. Ann. Chem 1953; 1: 582.
8. Torii S, Okumoto H, Sadakane M, He Xu L. Chem. Lett. 1991; 1673.
9. Murahashi S, Imada Y, Nishimura K. Tetrahedron 1994; 50: 2453.
10. Imada Y, Alper H. J. Org. Chem. 1996; 61: 6799.
11. Imada Y, Vasopollo G, Alper H. Org. Chem. 1996; 61: 7982.
12. El Ali B, El-Ghanam A, Fettouhi M, Tijani J. Tetrahedron Lett. 2000; 41: 5761.
13. Zargarian D, Alper H. Organometallics 1993; 12: 712.
14. Seayad A, Kelkar AA, Toniolo L, Chaudhari RV. J. Mol. Catal. 2000; 15: 47.
15. Hosokawa T, Murahashi SI. Acc. Chem. Res. 1990; 23: 49.
16. James DE, Stille JK. J. Am. Chem. Soc. 1976; 98: 1890.
17. Peter D, van Leeuwen PWNM. J. Chem. Soc. Dalton Trans. 1991; 1519.
18. Kawabata Y, Hayashi T, Ogata I. J. Chem. Soc. Dalton Trans. 1979; 462.
19. Konishi M, Kumada Y, Hayashi T. Tetrahedron Lett. 1979; 21: 1871.
20. Yamomato K, Momose S, Fumahashi M, Ebata S, Ohmura H, Komatsu H, Miyazawa M. Chem. Lett. 1994; 189.
21. Davies IW, Gerena L, Castonguay L, Senanayake HC, Larsen RD, Verhoeven TR, Reider JP. Chem. Commun. 1996; 1753.
22. Drent E, Arnoldy P, Budzelaar PHM. J. Organometal. Chem. 1994; 475: 57.
23. Bird CW. Chem. Rev. 1962; 62: 283.
24. Knifton JF. J. Mol. Catal. 1977; 2: 293.
25. Akao M, Sugawara S, Amino K, Inoue Y. J. Mol. Catal. 2000; 157: 117.
26. El Ali B, Tijani J, El-Ghanam A. Tetrahedron Lett. 2001; 42: 2385.
27. El Ali B, Tijani J, El-Ghanam A, Fettouhi M. Tetrahedron Lett. 2001; 42: 1567.
28. El Ali B, Tijani J, El-Ghanam A. J. Mol. Catal. 2002; 187: 17.
29. El Ali B, Alper H. J. Mol. Catal. 1991; 67: 29.
30. Seligson AL, Cowan RL, Troger WC. Inorg. Chem. 1991; 30: 3371.
31. Alper H, Maldonado MS, Lin IJB. J. Mol. Catal. 1988; 49: L27.