Allyl amines as ammonia equivalents in the preparation of anilines and heteroarylamines

Tetrahedron Letters

Volumn 39, Issue 11, 1998, Pages 1313-1316

  Jaime Figueroa, Saul ^a   Liu, Yanzhou ^a   Muchowski, Joseph M ^a   Putman, David G ^a  

^a ROCHE BIOSCIENCE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; AMINE; ANILINE; AROMATIC AMINE; PALLADIUM;

ARTICLE; CATALYSIS; SYNTHESIS;

EID: 0032510290     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10877-2     Document Type: Article

References (38)

1. 1. Larock, R. C. in "Comprehensive Organic Transformations." VCH Publishers Inc., New York, 1989, pp. 399-400.
2. 2. Hoffmann, R. W. in "Dehydrobenzene and Cycloalkynes." Verlag Chemie, Weinheim, 1967, pp. 115-122.
3. 3. Reinecke, M. G.Tetrahedron 1982, 38, 427.
4. 4. a) Giam, C. S. in "Pyridine and its Derivatives." Ed. by Abramovitch, R. A. Part 3. John Wiley and Sons, New York, 1974, pp 47-48.
5. b) Smally, R. K. in "Quinolines." Part 1. Ed. by Jones, G. John Wiley and Sons, New York, 1977, pp. 543-547.
6. c) Mathison, I. W., Solomons, W. E. in "Isoquinolines." Part 2. Ed. by Kathawala, F. G.; Coppola, G. M.; Schuster, H. F. John Wiley and Sons, New York, 1990, pp. 368-378.
7. 5. a) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem. Int. Ed. Engl. 1995, 34, 1348.
8. b) Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901.
9. c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133.
10. d) Wagaw, S.; Buchwald, S. L. J. Org. Chem 1996, 61, 7240.
11. e) Marcoux, J.-F.; Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1568.
12. f) Wolfe, J. P.; Buchwald, S. L. Tetrahedron Lett. 1997,38, 6359.
13. 6. a) Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc.1994, 116, 5969.
14. b) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609.
15. c) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708.
16. d) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217.
17. e) Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1264.
18. 7. a) Davydov, I. P.; Beletskaya Russ. Chem. Bull. 1995, 44, 1141.
19. b) Willoughby, C. A.; Chapman, K. T. Tetrahedron Lett. 1996, 37, 7181.
20. c) Ward, Y. D.; Farina, V. Tetrahedron Lett., 1996, 37, 6993.
21. c) Kang, S.-K.; Lee, H.-W.; Choi, W.-K.; Hong, R.-K.; Kim, J.-S. Synth. Commun. 1996, 26, 4219.
22. d) Kanbara, T.; Honma, A.; Hasegawa, K. Chem. Lett. 1996, 1135.
23. e) Zhao, S.-H.; Miller, A. K.; Berger, J.; Flippin, L. A. Tetrahedron Lett. 1996, 37, 4463.
24. f) Barta, N. S.; Pearson, W. H. Chemtracts: Org. Chem. 1996, 9, 88.
25. g) Beller, M.; Matthias, B.; Riermeier, T. H.; Reisinger, C.-P.; Herrmann, W. A. Tetrahedron Lett. 1997, 38, 2073.
26. h) Reddy, N. P.; Tanaka, M. Tetrahedron Lett. 1997, 38, 4807.
27. i) Darses, S.; Genêt, J.-P.; Brayer, J.-L.; Demoute, J.-P. Tetrahedron Lett. 1997, 38, 4393.
28. j) Beletskaya, I.P.; Bessermertnykh, A. G.; Guilard, R. Tetrahedron Lett. 1997, 38, 2287.
29. 8. We thank Professor L. E. Overman, U. C. Irvine for suggesting this point.
30. 9. Neither allyl-nor diallylamine have been previously reported to take part in palladium catalyzed animation of aryl halides.
31. 10. a) Laguzza, B. C.; Ganem, B.; Tetrahedron Lett. 1981, 22, 1483.
32. b) Picq, D.; Cottin, M.; Anker, D.; Pacheco, H. Tetrahedron Lett. 1983, 24, 1399.
33. c) Garro-Helion, F.; Merzouk, A.; Guibe, F. J. Org. Chem. 1993, 58, 6109.
34. d) Lemaire-Adoire, S.; Savignac, M.; Genêt, J.-P. Tetrahedron Lett. 1995, 36, 1267.
35. 11. Mono- and diallylamino products illustrated in Table 2 gave β-hydroxyaminopropyl derivatives when treated with 1 eq. of methanesulfonic acid, 10% Pd/C (w/w) in refluxing EtOH, e.g. (equation presented) No reaction occurs in the absence of palladium. As yet, we do not fully understand this interesting transformation.
36. 2, 1.4 eq. NaOtBu, 1.5 eq. N,N-diallylamine) was complete in 3 hours (77% yield). This result was surprising given that Buchwald reports 2-bromopyridine failed to give amination products using this catalyst (Ref. 5e).
37. 2). A mixture of 3-allylaminoquinoline (184 mg, 1 mmol), 10% Pd/C (184 mg) and methanesulfonic acid (64 μL, 1 mmol, 1 eq.) in 10 mL of absolute ethanol was heated for 2 h. TLC indicated the disappearance of starting 3-allylaminoquinoline. The reaction mixture was filtered through a Celite pad and concentrated in vacuo to give a solid residue. The residue was chromatographed on silica gel using hexanes/EtOAc (70: 30) to give 64 mg of a solid (45%). The product was spectroscopically identical to an authentic sample obtained from Aldrich Chem. Co.
38. 14. Wolfe, J. P.; Ahman, J.; Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6367.