Fast and regioselective Heck couplings with N-acyl-N-vinylamine derivatives

Journal of Organic Chemistry

Volumn 70, Issue 15, 2005, Pages 5997-6003

  Hansen, Anders Lindhardt ^a   Skrydstrup, Troels ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

BUTADIENE; HYDROGEN; HYDROLYSIS; ISOMERS; KETONES; OLEFINS; POSITIVE IONS;

BENZYLIC AMINES; HECK COUPLING; METHYL KETONES; REACTION TIMES;

AMINES;

2 ACYLAMINO 1,3 BUTADIENE; ACETONE; ALKENE; DIOXANE; N ACYL N VINYLAMINE DERIVATIVE; N VINYLCARBAMATE; N VINYLUREA; TOLUENESULFONIC ACID DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID VINYL ESTER; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYL TOSYLATE;

ARTICLE; CROSS COUPLING REACTION; HYDROGENATION; HYDROLYSIS; ISOMER; REACTION TIME; STEREOCHEMISTRY;

EID: 22344456684     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050669u     Document Type: Article

References (63)

1. For some relevant reviews, see: (a) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic Press: Orlando, 1985.
2. (b) Tsuji, J. Palladium Reagents and Catalysts: Innovation is Organic Synthesis; Wiley: Chichester, U.K., 1995.
3. (c) Brase, S.; de Meijere, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998; Chapter 3.
4. (c) Link, J. T.; Overman, L. E. In Metal-Catalyzed Cross-Coupling Reactions; Diederich F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998; Chapter 6.
5. (d) Transition Metal Catalyzed Reactions; Davis S. G., Murahashi, S.-I., Eds.; Blackwell Science, Oxford, 1999.
6. (e) Beletskaya, I.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
7. (f) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley & Sons: New York, 2002.
8. (f) Whitcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449.
9. (g) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules, 2nd ed.; University Science Books: Sausalito, CA, 1999; Chapter 4.6.
10. (h) Beller, M.; Riermeier, T. H.; Stark, G. In Transition Metals for Organic Synthesis; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Vol. 1, p 208.
11. Crisp, G. T. Chem. Soc. Rev. 1998, 27, 427.
12. For a few papers on the topic of insertion and regioselectivity, see: (a) Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc. 1991, 113, 1417.
13. (b) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2.
14. (c) Ludwig, M.; Stromberg, S.; Svensson, M.; Akermark, B. Organometallics 1999, 18, 970.
15. (d) Larhed, M.; Hallberg, A. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley & Sons: New York, 2002.
16. Cabri, W.; Candiani, I.; Bedeschi, A.; Santi, R. J. Org. Chem. 1992, 57, 3558.
17. For an excellent and historical account on factors controlling regioselectivity in the Heck reaction with electron-rich alkenes, see: Mo, J.; Xu, L.; Xiao, J. J. Am. Chem. Soc. 2005, 127, 751.
18. For an exception to this rule using ionic solvents, see ref 4.
19. (a) Andappan, M. M. S.; Nilsson, P.; von Schenck, H.; Larhed, M. J. Org. Chem. 2004, 69, 5212.
20. (b) Vallin, K. S. A.; Zhang, Q.; Larhed, M.; Curran, D. P.; Hallberg, A. J. Org. Chem. 2003, 68, 6639.
21. (c) Harrison, P.; Meek, G. Tetrahedron Lett. 2004, 45, 9277.
22. During the course of these investigations, Harrison and Meek (ref 6c) published a short and nonoptimized Heck coupling study with N-vinylacetamide, with coupling yields ranging from 24 to 69%.
23. For some recent examples, see: (a) Kessler, A.; Faure, H.; Petrel, C.; Ruat, M.; Dauban, P.; Dodd, R. H. Bioorg. Med. Chem. Lett. 2004, 14, 3345.
24. (b) Milkiewiez, K. L.; Marsilje, T. H.; Woodworth, R. P., Jr.; Bifulco, N., Jr.; Hangauer, M. J.; Hangauer, D. G. Bioorg. Med. Chem. Lett. 2000, 10, 483.
25. (c) Venkatachalam, T. K.; Sudbeck, E. A.; Mao, C.; Uckun, F. M. Bioorg. Med. Chem. Lett. 2000, 10, 2071.
26. (d) Dankwardt, S. M.; Martin, R. L.; Chan, C. S.; Van Wart, H. E.; Walker, K. A. M.; Delaet, N. G.; Robinson, L. A. Bioorg. Med. Chem. Lett. 2001, 11, 2085.
27. (e) Venkatachalam, T. K.; Qazi, S.; Samuel, P.; Uckun, F. M. Bioorg. Med. Chem. Lett. 2003, 13, 485.
28. (f) Auberson, Y. P.; Allegeier, H.; Bischoff, S.; Lingenhoehl, K.; Moretti, R.; Schmutz, M. Bioorg. Med. Chem. Lett. 2002, 12, 1099.
29. (g) Ashwood, V. A.; Field, M. J.; Horwell, D. C.; Julien-Larose, C.; Lewthwaite, R. A.; McCleary, S.; Pritchard, M. C.; Raphy, J.; Singh, L. J. Med. Chem. 2001, 44, 2276.
30. (h) Hanano, T.; Adachi, K.; Aoki, H.; Morimoto, H.; Naka, Y.; Hisadome, M.; Fukuda, T.; Sumichika, H. Bioorg. Med. Chem. Lett. 2000, 10, 881.
31. Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101.
32. For other approaches to the synthesis of N-acyl α-arylvinylamines, see: (a) Padwa, A.; Akiba, M.; Cohen, L. A.; MacDonald, G. J. Tetrahedron Lett. 1981, 22, 2435.
33. (b) Padwa, A.; Akiba, M.; Cohen, L. A.; MacDonald, G. J. J. Org. Chem. 1983,48, 695.
34. (c) Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem. 1998, 63, 6084.
35. (d) van den Berg, M.; Haak, R. M.; Minnaard, A. J.; De Vries, A. H. M.; Feringa, B. L. Adv. Synth. Catal. 2002, 344, 1003.
36. (e) Wallace, D. J.; Klauber, D. J.; Chen, C.-Y.; Volante, R. P. Org. Lett. 2003, 5, 4749.
37. N-Vinylacetamide is commerically available.
38. (a) Hart, R. Bull. Soc. Chim. Belg. 1956, 65, 291.
39. (b) Kirby, C.; Kroto, H. W. J. Mol. Spectrosc. 1978, 70, 216.
40. Jiang, L.; Job, G. E.; Klapars, A.; Buchwald, S. L. Org. Lett. 2003, 5, 3667.
41. See the Supporting Information.
42. For some examples, see: (a) Gürtler, C.; Buchwald, S. L. Chem. Eur. J. 1999, 5, 3107.
43. (b) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989.
44. (c) Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 13178.
45. Andappan, M. M. S.; Nilsson, P.; Larhed, M. Chem. Commun. 2004, 218.
46. dppp = 1,3-bis(diphenylphosphino)propane, dppf = 1,1′-bis- (diphenylphosphino)ferrocene, (R)-BINAP = (R)-2,2′-bis(diphenylphosphino)- 1,1′-binaphthyl, dmphen = 2,9-dimethyl-1,10-phenanthroline.
47. For an example of an asymmetric version of this hydrogenation step, see ref 6c.
48. Ohba, M.; Kawase, N.; Fujii, T. J. J. Am. Chem. Soc. 1996, 118, 8250.
49. For examples on the use of vinyl and aryl tosylates in palladium (0)-catalyzed coupling reactions, as well as oxidative addition studies, see: (a) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369.
50. (b) Fu, X.; Zhang, S.; Yin, J.; McAllister, T. L.; Jiang, S. A.; Tann, C.-H.; Thiruvengadam, T. K.; Zhang, F. Tetrahedron Lett. 2002, 43, 573.
51. (c) Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 8704.
52. (d) Roy, A. H.; Hartwig, J. F. Organometallics 2004, 23, 194.
53. (e) Klapars, A.; Campos, K. R.; Chen, C.-y.; Volante, R. P. Org. Lett. 2005, 7, 1185.
54. Not unexpectedly, aryl tosylates were not reactive to the coupling conditions developed.
55. Zhu, G.; Zhang, X. J. Org. Chem. 1998, 63, 25, 9590.
56. Harrison, P.; Meek, G. Tetrahedron Lett. 2004, 45, 50, 9277.
57. Berg, M.; Haak, R. M.; Minnaard, A. J.; Vries, A. H. M. de; Vries, J. G. de; Feringa, B. L. Adv. Synth. Catal. 344, 9, 2002, 1003.
58. Reetz, M. T.; Mehler, G.; Meiswinkel, A. Tetrahedron: Asymmetry 2004, 15, 14, 2165.
59. Hanano, Y.; Adachi, K.; Aoki, Y.; Morimoto, H.; Naka, Y.; Hisadome, M.; Fukuda, T.; Sumichika, H. Bioorg. Med. Chem. Lett. 2000, 10, 9, 881.
60. Lopez-Serrano, P.; Jongejan, J. A.; Rantwijk, F. van.; Sheldon, R. A. Tetrahedron: Asymmetry. 2001, 12, 2, 219.
61. Youshko, M. I.; Rantwijk, van F.; Sheldon, R. A. Tetrahedron: Asymmetry 2001, 12, 23, 3267.
62. Nakaminami, G. Bull. Chem. Soc. Jpn. 1962, 35, 1629.
63. Jalander, L.; Mattinen, J.; Oksanene, L.; Rosling, A. Synth. Commun. 1990, 20, 6, 881.