Phosphine ligands and nitrogen bases in the solvent-free Heck reaction ofbutenone with aryl iodides. A highly selective synthesis of benzalacetones

Arkivoc

Volumn 2003, Issue 8, 2003, Pages 58-66

  Cacchi, Sandro ^a   Fabrizi, Giancarlo ^a   Goggiamani, Antonella ^a  

^a Dipto Studi Chim Tecn Delle S   (Italy)

Author keywords

Benzalacetones; Conjugate addition; Heck reaction; Hydroarylation; Palladium

Indexed keywords

ALKANONE; BENZYLACETONE; BENZYLIDENEACETONE; BUTENONE; IODINE DERIVATIVE; LIGAND; NITROGEN DERIVATIVE; PALLADIUM COMPLEX; PHENYL IODIDE; PHOSPHINE DERIVATIVE; TRIS(2,4,6 TRIMETHOXYPHENYL)PHOSPHINE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ADDITION REACTION; ARTICLE; ARYLATION; CATALYSIS; HECK REACTION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 3242719450     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (59)

1. For recent references, see: (a) Alexakis, A.; March, S. J. Org. Chem. 2002, 67, 8753;
2. (b) Park, M. Y.; Yang, S. G.; Kim, Y. H. Heteroatom Chem. 2002, 13, 431;
3. (c) Andriamialisoa, Z.; Valla, A.; Cartier, D.; Labia, R. Helv. Chim. Acta 2002, 85, 2926;
4. (d) Shen, Y.; Feng, X.; Zhang, G.; Jiang, Y. Synlett 2002, 1353;
5. (e) Deng, Guisheng; T., X.; Qu, Z.; Wang, J. Angew. Chem., Internat. Ed. 2002, 41, 2773;
6. (f) Mizutani, H.; Degrado, S. J.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 779;
7. (g) Oi, S.; Honma, Y.; Inoue, Y. Org. Lett. 2002, 4, 667;
8. (h) Wang, Z.; Fetterly, B.; Verkade, J. G. J. Organomet. Chem. 2002, 646, 161.
9. See, for example: (a) Yamagami C.; Motohashi N.; Akamatsu M. Bioorg. Med. Chem. Lett. 2002, 12, 2281;
10. (b) Yamagami, C.; Kishida, N.; Ka, S.; Horiuchi, M.; Motohashi, N. Chem. Pharm. Bull. 1998, 46, 274;
11. (c) Motohashi, N.; Yamagami, C.; Tokuda, H.; Okuda, Y.; Ichiishi, E.; Mukainaka, T.; Nishino, H.; Saito, Y. Mut. Res. 2000, 464, 247;
12. (d) Motohashi, N.; Ashihara, Y.; Yamagami, C.; Saito, Y. Mut. Res. 2001, 474, 113;
13. (e) Yamagami, C.; Motohashi, N. Eur. J. Med. Chem. 2002, 37, 127.
14. (a) Cacchi, S.; Arcadi, A. J. Org. Chem. 1983, 48, 4236;
15. (b) Cacchi, S.; F. La Torre, G. Palmieri J. Organomet. Chem. 1984, 268, C48;
16. (c) Cacchi, S.; G. Palmieri Synlett 1984, 575;
17. (d) Arcadi, A.; Marinelli, F.; Cacchi, S. J. Organomet. Chem. 1986, 312, C27;
18. (e) Stokker, G. E. Tetrahedron Lett. 1987, 28, 3179;
19. (f) Wada, A.; Yasuda, H.; Kanatomo, S. Synthesis 1988, 771;
20. (g) Wolff, S.; Hoffmann, H. M. R. Synthesis 1988, 760;
21. (h) Hoffmann, M. H. R.; Schmidt, B.; Wolff, S. Tetrahedron 1989, 45, 6113;
22. (i) Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813;
23. (j) Konopelski, J. P.; Chu, K. S.; Negrete, G. R. J. Org. Chem. 1991, 56, 1355;
24. (k) Wada, A.; Ohki, K.; Nagai, S.; Kanatomo, S. J. Heterocyclic Chem. 1991, 28, 509;
25. (l) Friestad, G. K.; Braunchaud, B. P. Tetrahedron Lett. 1995, 36, 7047;
26. (m) Hagiwara, H.; Eda, Y.; Morohashi, K.; Suzuki, T.; Ando, M.; Ito, N. Tetrahedron Lett. 1998, 39, 4055;
27. (n) Cacchi, S.; Fabrizi, G., Gasparrini, F.; Pace, P.; Villani, C. Synlett 2000, 650.
28. 4 under our usual conditions produced 3a, 4a and 3,3-diphenyl-2-butanone in 13, 21 and 30% yield, respectively.
29. (a) Cacchi, S.; G. Fabrizi, Gasparrini, F.; Pace, P.; Villani, C. Synlett 1999, 345;
30. (b) Battistuzzi, G.; Cacchi, S.; Fabrizi, G. Synlett 2002, 439;
31. (c) Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Moreno-Manas, Vallribera, A. Tetrahedron Lett. 2002, 43, 5537.
32. For reviews on solvent-free reactions, see: (a) Dittmer, D. C. Chem. Ind. 1997, 779;
33. (b) Metzger, J. O. Angew. Chem., Internat. Ed. 1998, 37, 2975;
34. (c) Loupy, A.; Petit, Alain; H., J.; Texier-Boullet, F.; Jacquault, P.; Mathe, D. Synthesis 1998, 1213;
35. (d) Tanaka, K.; Toda, F. Chem. Rev. 2000, 100, 1025;
36. (e) Diaz-Ortiz, A.; de la Hoz, A.; Langa, F. Green Chem. 2000, 2, 165;
37. (f) Varma, R. S. Pure Appl. Chem. 2001, 73, 193.
38. (a) Cabri, W.; Candiani, I.; De Bernardis, S.; Francalanci, F.; Penco, S. J. Org. Chem. 1991, 56, 5796;
39. (b) Laschat, S.; Narjes, F.; Overman, L.E. Tetrahedron 1994, 50, 347;
40. (c) Arcadi, A.; Cacchi, S.; Fabrizi, G.; Marinelli, F.; Pace, P. Tetrahedron 1996, 52, 6983.
41. For some examples of phosphine displacement by amines in palladium complexes, see: (a) Widenhoefer, R. A.; Buchwald, S. L. Organometallics 1996, 15, 3534;
42. (b) Khong, H. A.; Widenhoefer, R. A. Organometallics 1997, 36, 2610.
43. For some leading references on palladium enolates, see: (a) Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011;
44. (b) Minami, I.; Nisar, M.; Yuhara, M.; Shimizu, I.; Tsuji, J. Synthesis 1987, 992;
45. (c) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J. Am. Chem. Soc. 1989, 111, 4126;
46. (d) Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30
47. (e) Ogoshi, S.; Morimoto, T.; Nishio, K.-I.; Ohe, K.; Murai, S. J. Org. Chem. 1993, 58, 9;
48. (f) Soeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463;
49. (g) Garg, N.; Larhed, M.; Hallberg, A. J. Org. Chem. 1998, 63, 4158;
50. (h) Shim, J.-G.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1998, 63, 8470;
51. (i) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473;
52. (j) Albéniz, A. C.; Catalina, N. M.; Espinet, P.; Redón, R. Organometallics 1999, 18, 5571;
53. (k) Lei, A.; Zhang, X. Tetrahedron Lett. 2002, 43, 2525.
54. 3 has been reported to create coordinatively unsaturated palladium species: Paul, F.; Patt, J.; Hartwig, J.F. Organometallics 1995, 14, 3030.
55. Wada, M.; Higashizaki, S. J. Chem. Soc., Chem. Comm. 1984, 482.
56. Tolman, C.A. Chem. Rev. 1977, 77, 313.
57. Elias, G.; Rao, M. Eur. J. Med. Chem. 1988, 23, 379.
58. Evans, D. A.; Gauchet-Prunet, J. A.; Carreira, E. M.; Charette, A. B. J. Org. Chem. 1991, 56, 741.
59. Edwards, M. L.; Ritter, H. W.; Stemerick, D. M.; Stewart, K. T. J. Med. Chem. 1983, 26, 431.