Synthesis of α,β-unsaturated ketones by rhodium-catalyzed carbonylative arylation of internal alkynes with arylboronic acids

Synlett

Volumn , Issue 17, 2008, Pages 2587-2592

  Ku̧, Melih ^a   Artok, Özge Aksin ^a   Ziyanak, Firat ^a   Artok, Levent ^a  

^a IZMIR INSTITUTE OF TECHNOLOGY   (Turkey)

Author keywords

Alkynes; Boron; Carbonylation; Enones; Rhodium

Indexed keywords

1 (4 METHOXYPHENYL) 2 METHYL 3 PHENYLPROP 2 EN 1 ONE; 1 (4 METHOXYPHENYL) 2 PHENYLHEX 2 EN 1 ONE; 1 (4 METHOXYPHENYL) 2 PROPYLHEX 2 EN 1 ONE; 1 (4 METHOXYPHENYL) 2,3 DIPHENYLPROP 2 EN 1 ONE; 1 PHENYL 2 PROPYLHEX 2 EN 1 ONE; 1,2,3 TRIPHENYLPROP 2 EN 1 ONE; 2 BENZYLIDENE 1 (4 METHOXYPHENYL)PENTAN 1 ONE; 2 METHYL 1,3 DIPHENYLPROP 2 EN 1 ONE; 2 PROPYL 1 4 TOLYLHEX 2 EN 1 ONE; 2,3 DIPHENYL 1 3 TOLYLPROP 2 EN 1 ONE; 2,3 DIPHENYL 1 4 TOLYLPROP 2 EN 1 ONE; ACETYLENE DERIVATIVE; ALKYNE; ALPHA BETA UNSATURATED KETONE DERIVATIVE; ARYLBORONIC ACIDS; BORONIC ACID DERIVATIVE; CARBON DIOXIDE; DIARYL ACETYLENE DERIVATIVE; DIPHENYL ACETYLENE; KETONE; METHYL 4 (4 METHOXYPHENYL) 3 BUTYL 4 OXOBUT 2 ENOATE; METHYL 4 (4 METHOXYPHENYL) 3 METHYL 4 OXOBUT 2 ENOATE; RHODIUM; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; ARYLATION; CARBONYLATION; CATALYSIS; CONTROLLED STUDY; ISOMER;

EID: 55549108402     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/3-2008-1078047     Document Type: Article

References (35)

1. Aksin, Ö.; Dege, N.; Artok, L.; Turkmen, H.; Çetinkaya, B. Chem. Commun. 2006, 3187.
2. (a) Sauthier, M.; Castanet, Y.; Mortreux, A. Chem. Commun. 2004, 1520.
3. (b) Chochois, H.; Sauthier, M.; Maerten, E.; Castanet, Y.; Mortreux, A. Tetrahedron 2006, 62, 11740.
4. (c) Menard, F.; Weise, C. F.; Lautens, M. Org. Lett. 2007, 9, 5335.
5. (d) Dheur, J.; Sauthier, M.; Castanet, Y.; Mortreux, A. Adv. Synth. Catal. 2007, 349, 2499.
6. (a) Willis, M. C.; Randell-Sly, H. E.; Woodward, R. L.; Steven, J.; McNally, S. J.; Currie, G. S. J. Org. Chem. 2006, 71, 5291.
7. (b) Tanaka, K.; Shibata, Y.; Suda, T.; Hagiwara, Y.; Hirano, M. Org. Lett. 2007, 9, 1215.
8. (c) Imai, M.; Tanaka, M.; Tanaka, K.; Yamamoto, Y.; Imai-Ogata, N.; Shimowatari, M.; Nagumo, S.; Kawahara, N.; Suemune, H. J. Org. Chem. 2004, 69, 1144.
9. (d) Jun, C.-H.; Lee, H.; Hong, J.-B.; Kwon, B. I. Angew. Chem. Int. Ed. 2002, 41, 2146.
10. (e) Moxham, G. L.; Randell-Sly, H. E.; Brayshaw, S. K.; Woodward, R. L.; Weller, A. S.; Willis, M. C. Angew. Chem. Int. Ed. 2006, 45, 7618.
11. (f) Tanaka, K.; Tanaka, M.; Suemune, H. Tetrahedron Lett. 2005, 46, 6053.
12. (g) Willis, M. C.; Sapmaz, S. Chem. Commun. 2001, 2558.
13. (h) Jun, C.-H.; Jo, E.-A.; Park, J.-W. Eur. J. Org. Chem. 2007, 1869.
14. (i) Stemmlera, R. T.; Bolma, C. Adv. Synth. Catal. 2007, 349, 1185.
15. (j) Imai, M.; Tanaka, M.; Nagumo, S.; Kawahara, N.; Suemune, H. J. Org. Chem. 2007, 72, 2543.
16. (k) Rueda, X. Y.; Castillón, S. J. Organomet. Chem. 2007, 692, 1628.
17. (l) Lochow, C. F.; Miller, R. G. J. Am. Chem. Soc. 1976, 98, 1281.
18. (m) Kokubo, K.; Matsumasa, K.; Miura, M.; Nomura, M. J. Org. Chem. 1997, 62, 4564.
19. (n) Miura, M.; Nomura, M. J. Synth. Org. Chem. Jpn. 2000, 58, 578.
20. (o) Kokubo, K.; Matsumasa, K.; Nishinaka, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1999, 72, 303.
21. (p) Marder, T. D.; Roe, D. C.; Milstein, D. Organometallics 1988, 7, 1451.
22. Other acylation reagents used: (a) Hydrogenative aroylation with an anhydride: Hong, Y.-T.; Barchuk, A.; Krische, M. J. Angew. Chem. Int. Ed. 2006, 45, 6885.
23. (b) Hydroacylation of ethylene with acyl halides: Schwartz, J.; Cannon, J. B. J. Am. Chem. Soc. 1974, 96, 4721.
24. Other metal catalysis - Ir catalyzed: (a) Nishinaka, Y.; Satoh, T.; Miura, M.; Morisaka, H.; Nomura, M.; Matsui, H.; Yamaguchi, C. Bull. Chem. Soc. Jpn. 2001, 74, 1727. Ni catalyzed:
25. (b) Tsuda, T.; Kiyoi, T.; Saegusa, T. J. Org. Chem. 1990, 55, 2555. Ru catalyzed:
26. (c) Kondo, T.; Tsuji, Y.; Watanabe, Y. Tetrahedron Lett. 1987, 28, 6229.
27. (d) Kondo, T.; Akazome, M.; Tsuji, Y.; Watanabe, Y. J. Org. Chem. 1990, 55, 1286. Co catalyzed:
28. (e) Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 3165.
29. 3): δ = 2.40 (s, 3 H), 7.06-7.38 (m, 13 H), 7.64 (d, J = 7.6 Hz, 1 H), 7.68 (s, 1 H).
30. (a) Duke, P. J.; Boykin, D. W. Jr. J. Org. Chem. 1972, 37, 1436.
31. (b) Black, W. B.; Lutz, R. E. J. Am. Chem. Soc. 1953, 75, 5990.
32. (c) Mittal, S.; Durani, S.; Kapil, R. S. J. Med. Chem. 1985, 28, 492.
33. See Figure 1.
34. Hayashi, T.; Inoue, K.; Taniguchi, N.; Ogasawara, M. J. Am. Chem. Soc. 2001, 123, 9918.
35. Rhodium(I)-catalyzed reaction of 2-bromo-substituted phenylboronic acids with alkynes under CO atmosphere leading to indenone structures was reported. See: Harada, Y.; Nakanishi, J.; Fujihara, H.; Tobisu, M.; Fukumoto, Y.; Chatani, N. J. Am. Chem. Soc. 2007, 29, 5766.