N-heterocyclic carbene-catalyzed nucleophilic aroylation of fluorobenzenes

Journal of Organic Chemistry

Volumn 73, Issue 6, 2008, Pages 2420-2423

  Suzuki, Yumiko ^a   Ota, Shinya ^a   Fukuta, Yoshinori ^a   Ueda, Yuki ^a   Sato, Masayuki ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYSTS;

AROMATIC ALDEHYDES; FLUOROBENZENES; NUCLEOPHILIC SUBSTITUTION; POLYSUBSTITUTED BENZOPHENONES;

BENZENE;

BENZALDEHYDE; BENZENE DERIVATIVE; BENZOIN; CARBENOID; FLUOROBENZENE; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE;

AMIDATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; POLYMERIZATION; RING OPENING; SYNTHESIS; TRANSESTERIFICATION;

BENZALDEHYDES; BENZOPHENONES; CATALYSIS; FLUOROBENZENES; HETEROCYCLIC COMPOUNDS; HYDROCARBONS; METHANE;

EID: 41849103107     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7023569     Document Type: Article

References (64)

1. N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2006.
2. (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
3. (b) Díez-González, S.; Nolan, S. P. Coord. Chem. Rev. 2007, 251, 874.
4. (c) N-Heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F., Ed.; Topics in Organometallic Chemistry, Vol. 28; Springer-Verlag: Berlin/Heidelberg, Germany, 2007.
5. For reviews, see: (a) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534.
6. (b) Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem., Int. Ed. 2004, 43, 5130.
7. (c) Marion, N.; Díez-González, S.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988.
8. (a) Ukai, T.; Tanaka, R.; Dokawa, T. J. Pharm. Soc. Jpn. 1943, 63, 296.
9. (b) Ukai, T.; Dokawa, T.; Tsubokawa, S. J. Pharm. Soc. Jpn. 1944, 64, 7A, 3.
10. (c) Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719.
11. (d) Enders, D.; Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743.
12. (e) Hachisu, Y.; Bode, J. W.; Suzuki, K. J. Am. Chem. Soc. 2003, 125, 8432.
13. (a) Stetter, H.; Kuhlmann, H. Chem. Ber. 1976, 109, 2890.
14. (b) Stetter, H.; Kuhlmann, H. Org. React. 1991, 40, 407.
15. (c) Enders, D.; Breuer, K.; Runsink, J.; Teles, J. H. Helv. Chim. Acta 1996, 79, 1899.
16. (d) Kerr, M. S.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 10298.
17. (e) Mattson, A. E.; Bharadwaj, A. R.; Scheidt, K. A. J. Am. Chem. Soc. 2004, 126, 2314.
18. For selected examples of transesterification and amidation, see: (a) Grasa, G. A.; Kissling, R. M.; Nolan, S. P. Org. Lett. 2002, 4, 3583.
19. (b) Nyce, G. W.; Lamboy, J. A.; Connor, E. F.; Waymouth, R. M.; Hedrick, J. L. Org. Lett. 2002, 4, 3587.
20. (c) Grasa, G. A.; Singh, R.; Nolan, S. P. Synthesis 2004, 971.
21. (d) Kano, T.; Sasaki, K.; Maruoka, K. Org. Lett. 2005, 7, 1347.
22. (e) Movassaghi, M.; Schmidt, M. A. Org. Lett. 2005, 7, 2453.
23. For selected examples of living ring-opening polymerization, see: (a) Connor, E. F.; Nyce, G. W.; Myers, M.; Möck, A.; Hedrick, J. L. J. Am. Chem. Soc. 2002, 124, 914.
24. (b) Coulembier, O.; Dove, A. P.; Pratt, R. C.; Sentman, A. C.; Culkin, D. A.; Mespouille, L.; Dubois, P.; Waymouth, R. M.; Hedrick, J. L. Angew. Chem., Int. Ed. 2005, 44, 4964.
25. For selected examples of homoenolate reaction, see: (a) Orduna, A.; Zepeda, L. G.; Tamariz, J. Synthesis 1993, 375.
26. (b) Collins, I. J. Chem. Soc., Perkin Trans. 1 1998, 1869.
27. (c) Burstein, C.; Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205.
28. (d) Sohn, S. S.; Rosen, E. L.; Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370.
29. (e) Fisher, C.; Smith, S. W.; Powel, D. A.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 1472.
30. (f) Nair, V.; Vellalath, S.; Poonoth, M.; Suresh, E. J. Am. Chem. Soc. 2006, 128, 8736.
31. (g) Nair, V.; Poonoth, M.; Vellalath, S.; Suresh, E.; Thirumalai, R.; J. Am. Chem. Soc. 2006, 128, 8964.
32. For other examples, see: (a) Reynolds, N.; Read de Alaniz, J.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 9518.
33. (b) Song, J. J.; Tan, Z.; Reeves, J. T.; Gallou, F.; Yee, N. K; Senanayake, C. H. Org. Lett. 2005, 7, 2193.
34. (c) Song, J. J.; Gallou, F.; Reeves, J. T.; Tan, Z.; Yee, N. K; Senanayake, C. H. J. Org. Chem. 2006, 71, 1273.
35. (d) Fukuda, Y.; Maeda, Y.; Ishii, S.; Kondo, K.; Aoyama, T. Synthesis, 2006, 589.
36. (e) Fukuda, Y.; Maeda, Y.; Kondo, K.; Aoyama, T. Chem. Pharm. Bull. 2006, 54, 397.
37. (f) Fukuda, Y.; Maeda, Y.; S.; Kondo, K.; Aoyama, T. Synthesis 2006, 1937.
38. (g) Kano, T.; Sasaki, K.; Konishi, T.; Mii, H.; Maruoka, K.; Tetrahedron Lett. 2006, 47, 4615.
39. (h) Chan, A.; Scheidt, K. A. J. Am. Chem. Soc. 2006, 128, 4558.
40. (i) Wu, J.; Sun, X.; Ye, S.; Sun, W. Tetrahedron Lett. 2006, 47, 4813.
41. (j) Zeitler, K. Org. Lett. 2006, 8, 637.
42. (k) Sohn, S. S.; Bode, J. W. Angew. Chem., Int. Ed. 2006, 44, 6021.
43. (l) He, M.; Struble, J. R.; Bode, J. W.; J. Am. Chem. Soc. 2006, 128, 8418.
44. (m) Thomson, J. E.; Rix, K.; Smith, A. D.; Org. Lett. 2006, 8, 3785.
45. (n) He, J.; Zheng, J.; Liu, J.; She, X.; Pan, X.; Org. Lett. 2006, 8, 4637.
46. (o) Maki, B. E.; Chan, A.; Phillips, E. M.; Scheidt, K. A.; Org. Lett. 2007, 9, 371.
47. (p) Song, J. J.; Tan, Z.; Reeves, J. T.; Yee, N. K.; Senanayake, C. H. Org. Lett. 2007, 9, 1013.
48. Miyashita, A.; Suzuki, Y.; Kobayashi, M.; Kuriyama, N.; Higashino, T. Heterocycles 1996, 43, 509.
49. (a) Miyashita, A.; Suzuki, Y.; Okumura, Y.; Higashino, T. Chem. Pharm. Bull. 1996, 44, 252.
50. (b) Miyashita, A.; Suzuki, Y.; Okumura, Y.; Iwamoto, K.; Higashino, T. Chem. Pharm. Bull. 1998, 46, 6.
51. (a) Miyashita, A.; Matsuda, H.; Iijima, C.; Higashino, T.; Chem. Pharm. Bull. 1990, 38, 1147.
52. (b) Miyashita, A.; Matsuda, H.; Suzuki, Y.; Iwamoto, K.; Higashino, T. Chem. Pharm. Bull. 1994, 42, 2017-2022.
53. (c) Miyashita, A.; Suzuki, Y.; Iwamoto, K.; Higashino, T. Chem. Pharm. Bull. 1994, 42, 2633-2635.
54. (d) Miyashita, A.; Suzuki, Y.; Nagasaki, I.; Ishiguro, C.; Iwamoto, K.; Higashino, T. Chem. Pharm. Bull. 1997, 45, 1254-1258.
55. (e) Miyashita, A.; Obae, K.; Suzuki, Y.; Iwamoto, K.; Oishi, E.; Higashino, T. Hetrocycles 1997, 45, 2159-2173.
56. (f) Miyashita, A.; Suzuki, Y.; Iwamoto, K.; Higashino, T. Chem. Pharm. Bull. 1998, 46, 390-399.
57. (g) Miyashita, A.; Suzuki, Y.; Iwamoto, K.; Oishi, E.; Higashino, T. Heterocycles 1998, 49, 405-413.
58. Miyashita, A.; Matsuda, H.; Higashino, T. Chem. Pharm. Bull. 1992, 40, 2627.
59. Suzuki Y.; Toyota T.; Imada F.; Sato M.; Miyashita A. Chem. Commun. 2003, 1314.
60. Suzuki, Y.; Toyota, T.; Miyashita, A.; Sato, M. Chem. Pharm. Bull. 2006, 54, 1653.
61. (a) Suzuki, Y.; Yamauchi, K.; Muramatsu, K.; Sato, M. Chem. Commun. 2004, 2770.
62. (b) Suzuki, Y.; Muramatsu, K.; Yamauchi, K.; Sato, M. Tetrahedron 2006, 62, 302.
63. Suzuki, Y.; Bakar, A.M.D.; Muramatsu, K.; Sato, M. Tetrahedron, 2006, 62, 4227.
64. Beilstein Handbook of Organic Chemistry; Springer: Heidelberg, Germany, 1925; Vol. 7, 426.