Nickel-NHC-catalyzed α-arylation of acyclic ketones and amination of haloarenes and unexpected preferential N-arylation of 4-aminopropiophenone

Journal of Organic Chemistry

Volumn 72, Issue 14, 2007, Pages 5069-5076

  Matsubara, Kouki ^a   Ueno, Keita ^a   Koga, Yuji ^a   Hara, Kenji ^a  

^a FUKUOKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4-AMINOPROPIOPHENONE; AMINOPROPIOPHENONE; N-ARYLATION;

AMINATION; AMINES; CATALYSIS; LIGANDS; NICKEL;

KETONES;

4 AMINOPROPIOPHENONE; CARBENOID; HALIDE; KETONE DERIVATIVE; NICKEL; NICKEL COMPLEX; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

AMINATION; ARTICLE; ARYLATION; CATALYST; REACTION ANALYSIS; SYNTHESIS;

AMINATION; CATALYSIS; HALOGENS; HYDROCARBONS, CYCLIC; KETONES; MOLECULAR STRUCTURE; NICKEL;

EID: 34447324382     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070313d     Document Type: Article

References (49)

1. (a) Modern Organonickel Chemistry; Tamaru, Y., Ed.; Wiley-VCH: Weinheim, Germany, 2005.
2. (b) Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12.
3. (c) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1469.
4. (d) Stanforth, S. P. Tetrahedron 1998, 54, 263-303.
5. (e) Negishi, E. Acc. Chem. Res. 1982, 15, 340-348.
6. (a) Palladium in Organic Synthesis; Tsuji, J., Ed.; Springer: Berlin, 2005.
7. (b) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., De Meijere, A., Eds.; Wiley: New York, 2002.
8. (c) Perspectives in Organopalladium Chemistry for the XXI Century; Tsuji, J., Ed.; Elsevier Science: Amsterdam, 1999.
9. Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234-245.
10. (b) Bolm, C.; Hildebrand, J. P.; Muniz, K.; Hermanns, N. Angew. Chem., Int. Ed. 2001, 40, 3284-3308.
11. (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
12. (b) Müller, T. E.; Beller, M. Chem. Rev. 1998, 98, 675-703.
13. (a) Spielvogel, D. J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 3500-3501.
14. (b) Spielvogel D. J.; Davis, W. M.; Buchwald, S. L. Organometallics 2002, 21, 3833-3836.
15. (c) Chen, G.; Kwong, F. Y.; Chan, H. O.; Yub, W.- Y.; Chan, A. S. C. Chem. Commun. 2006, 1413-1415.
16. (d) Cristau, H. J.; Vogel, R.; Taillefer, M.; Gadras, A. Tetrahedron. Lett. 2000, 41, 8457-8460.
17. (e) Semmelhack, M. F.; Stauffer R. D.; Rogerson, T. D. Tetrahedron Lett. 1973, 4519-4522.
18. (f) Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833-4835.
19. (a) Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6054-6058.
20. (b) Desmarets, C.; Schneider, R.; Fort, Y. J. Org. Chem. 2002, 67, 3029-3036 and references therein.
21. (c) Bricout, H.; Carpentier, J. -F.; Mortreux, A. Tetrahedron 1998, 54, 1073-1084.
22. (d) Kelly, R. A., III; Scott, N. M.; Díez-González, S.; Stevens, E. D.; Nolan, S. P. Organometallics 2005, 24, 3442-3447.
23. (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309.
24. (b) Weskamp, T.; Böhm, V. P. W.; Herrmann, W. A. J. Organomet. Chem. 2000, 600, 12-22.
25. (c) Bourissou, D.; Guerret, O.; Gabba, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91.
26. (d) Herrmann, W. A.; Schütz, J.; Frey, G. D.; Herdtweck, E. Organometallics 2006, 25, 2437-2448.
27. (e) Kantchev, E. A. B.; O' Brien, C. J.; Organ, M. G. Angew. Chem., Int. Ed. 2007, 46, 2768-2813.
28. Marion, N.; Ecarnot, E. C.; Navarro, O.; Amoroso, D.; Bell, A.; Nolan, S. P. J. Org. Chem. 2006, 71, 3816-3821.
29. Matsubara, K.; Ueno, K.; Shibata, Y. Organometallics 2006, 25, 3422-3427.
30. (a) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370.
31. (b) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473-1478.
32. Matsubara, K.; Senju, M.; Okazaki, H. J. Organomet. Chem. 2006, 691, 3693-3699.
33. 5c We considered that the steric demand around the α-position of the carbonyl group might induce such a low reactivity in comparison with that of the cyclic analogues.
34. (a) Ehrentraut, A.; Zapf, A.; Beller, M. Adv. Synth. Catal. 2002, 344, 209-217.
35. (b) Moradi, W. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7996-8002.
36. The reduced product, anisole, did not form in the reaction. The C-O bond activation of the anisole derivatives was also anticipated and is shown in the following report on nickel-catalyzed Grignard coupling: Dankwardt, J. W. Angew. Chem., Int. Ed. 2004, 43, 2428-2432.
37. 3 palladium complexes were reported; see: Herrmann, W. A.; Böhm, V. P. W.; Gstöttmayr, C. W. K.; Grosche, M.; Reisinger, C. -P.; Weskamp, T. J. Organomet. Chem. 2001, 617-618, 616-628.
38. Ackermann, L.; Born, R. Angew. Chem., Int. Ed. 2005, 44, 2444-2447.
39. Louie, J.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 11695-11696.
40. Hartwig, J. F.; Richards, S.; Baranano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626-3633.
41. (a) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217-7218.
42. (b) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216.
43. (a) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852-860.
44. (b) Yamashita, M.; Vicario, J. V. C.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 16347-16360.
45. Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 5816-5817.
46. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 3694-3703.
47. For examples of C- and O-bound nickel enolate complexes, see: (a) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30-44.
48. (b) Cámpora, J.; Maya, C. M.; Palma, P.; Carmona, E.; Gutiérrez-Puebla, E.; Ruiz, C. J. Am. Chem. Soc. 2003, 125, 1482-1483.
49. Gupton, J. T.; Idoux, J. P.; Baker, G.; Colon, C.; Crews, A. D.; Jurss, C. D.; Rampi, R. C. J. Org. Chem. 1983, 48, 2933-2936.