Palladium-catalyzed acylation and/or homo-coupling of aryl- and alkyl-acetylenes

Tetrahedron

Volumn 67, Issue 38, 2011, Pages 7386-7391

  Perrone, Serena ^a   Bona, Fabio ^a   Troisi, Luigino ^a  

^a UNIVERSITY OF SALENTO   (Italy)

Author keywords

Acetylenic ketones; Acylation; Diynes; Homo coupling; Palladium

Indexed keywords

1 (4 ETHYNYLPHENYL)HEX 4 EN 1 YN 3 ONE; 1 (4 METHOXYPHENYL)HEX 4 EN 1 YN 3 ONE; 4 (3 OXO 4 PHENYLBUT 1 YNYL)BENZONITRILE; 4 (3 OXOHEX 4 EN 1 YNYL)BENZONITRILE; 4 (4 ETHYNYLPHENYL) 1 PHENYLBUT 3 YN 2 ONE; 4 (4 METHOXYPHENYL) 1 PHENYLBUT 3 YN 2 ONE; 5 METHYL 1 PHENYLHEX 4 EN 1 YN 3 ONE; ACETYLENE DERIVATIVE; ACETYLENIC KETONE; ALKYNE DERIVATIVE; ALLYL HALIDE; BENZYL HALIDE; CARBON MONOXIDE; HALIDE; KETONE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; CONJUGATE; CROSS COUPLING REACTION; DIMERIZATION; NUCLEOPHILICITY; PALLADIUM CATALYZED ACYLATION; PRIORITY JOURNAL;

EID: 80051783356     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.07.032     Document Type: Article

References (48)

1. F. Bohlmann, F.T. Burkhart, and C. Zero Naturally Occurring Acetylenes 1973 Academic London
2. L. Hansen, and P.M. Boll Phytochemistry 25 1986 285 293
3. H. Matsunaga, M. Katano, H. Yamamoto, H. Fujito, M. Mori, and K. Takata Chem. Pharm. Bull. 38 1990 3480 3482
4. P. Siemsen, R.C. Livingston, and F. Diederich Angew. Chem. 112 2000 2740 2767
5. C. Glaser Ber. Dtsch. Chem. Ges. 2 1869 422 424
6. A.S. Hay J. Org. Chem. 27 1962 3320 3323
7. I.D. Campbell, and G. Eglinton Org. Synth. 45 1965 39 42
8. J. Li, and H. Jiang Chem. Commun. 1999 2369 2370
9. R. Salazar, L. Fomina, and S. Fomine Polym. Bull. 47 2001 151 158
10. A. Sharifi, M. Mirzaei, and M.R. Naini-Jamal J. Chem. Res. 2002 628 630
11. J.S. Yadav, B.V.S. Reddy, K.B. Reddy, K.U. Gayathri, and A.R. Prasad Tetrahedron Lett. 44 2003 6493 6496
12. L. Wang, J. Yan, P. Li, M. Wang, and C. Su J. Chem. Res. 2005 112 115
13. X. Lu, Y. Zhang, C. Luo, and Y. Wang Synth. Commun. 36 2006 2503 2511
14. K. Kamata, S. Yamaguchi, M. Kotani, K. Yamaguchi, and N. Mizuno Angew. Chem. 120 2008 2441 2444
15. K. Yamaguchi, K. Kamata, S. Yamaguchi, M. Kotani, and N. Mizuno J. Catal. 258 2008 121 130
16. T. Oishi, T. Katayama, K. Yamaguchi, and N. Mizuno Chem. - Eur. J. 15 2009 7539 7542
17. X. Meng, C. Li, B. Han, T. Wang, and B. Chen Tetrahedron 66 2010 4029 4031
18. E. Shirakawa, Y. Nakao, Y. Murota, and T. Hiyama J. Organomet. Chem. 670 2003 132 136
19. E.R.H. Jones, L. Skattebol, and M.C. Whiting J. Chem. Soc. 1956 4765 4768
20. T. Fukumaru, H. Awata, N. Hamma, and T. Komatsu Agric. Biol. Chem. 39 1975 519 527
21. M. Bakherad, A. Keivanloo, B. Bahramian, and S. Jajarmi Synlett 2011 311 314
22. M.T. Rahman, T. Fukuyama, N. Kamata, M. Sato, and I. Ryu Chem. Commun. 2006 2236 2238
23. L. Troisi, L. De Vitis, C. Granito, T. Pilati, and E. Pindinelli Tetrahedron 60 2004 6895 6900
24. L. Troisi, R. Ronzini, C. Granito, E. Pindinelli, A. Troisi, and T. Pilati Tetrahedron 62 2006 12064 12070
25. L. Troisi, C. Granito, and E. Pindinelli Tetrahedron 64 2008 11632 11640
26. L. Troisi, C. Granito, F. Rosato, and V. Videtta Tetrahedron Lett. 51 2010 371 373
27. Tommasi, S.; Perrone, S.; Rosato, F.; Salomone, A.; Troisi, L. Synthesis, submitted for publication.
28. G.A. Ardizzoia, S. Brenna, S. Cenini, G. La Monica, N. Ma sciocchi, and A. Maspero J. Mol. Catal. A: Chem. 333 2003 204 205
29. G. Hilt, T. Vogler, W. Hess, and F. Galbiati Chem. Commun. 2005 1474 1475
30. G. Hilt, C. Hengst, and W. Hess Eur. J. Org. Chem. 2008 2293 2297
31. G.A. Tolstikov, F.K. Valitov, and A.V. Kuchin Zh. Obshch. Khim. 53 1983 2284 2286
32. M. Tanaka, and T. Kobayashi Jpn. Kokai Tokkyo Koho 1985 5
33. F. Bardone-Gaudemar Ann. Chim. (Paris) 3 1958 52 107
34. D. Manoiu, M. Manoiu, I.G. Dinulescu, and M. Avram Rev. Roum. Chim. 30 1985 223 227
35. N. Kakusawa, K. Yamaguchi, and J. Kurita J. Organomet. Chem. 690 2005 2956 2966
36. S. Adimurthy, C.C. Malakar, and U. Beifuss J. Org. Chem. 74 2009 5648 5651
37. V. Kumar, A. Chipeleme, and K. Chibale Eur. J. Org. Chem. 1 2008 43 46
38. S. Guha, C.C. Frazier, P.L. Porter, K. Kang, and S.E. Finberg Opt. Lett. 14 1989 952 954
39. M. Bassetti, C. Pasquini, A. Raneri, and D. Rosato J. Org. Chem. 72 2007 4558 4561
40. D.A. Ben-Efraim Tetrahedron Lett. 11 1967 957 960
41. H.C. Brown, N.G. Bhat, and D. Bassavaiah Isr. J. Chem. 24 1984 72 75
42. F.V. Singh, M. Weber, R.C. Guadagnin, and H.A. Stefani Synlett 2008 1889 1893
43. W.T. Boese, and A.S. Goldman Organometallics 10 1991 782 786
44. F.A. Selimov, O.G. Rutman, and U.M. Dzhemilev Zh. Org. Khim. 19 1983 1853 1856
45. A. Geny, N. Agenet, L. Iannazzo, M. Malacria, C. Aubert, and V. Gandon Angew. Chem., Int. Ed. 48 2009 1810 1813
46. V. Cadierno, S.E. Garcia-Garrido, and J. Gimeno J. Am. Chem. Soc. 128 2006 15094 15095
47. A. Joosten, M. Soueidan, C. Denhez, D. Harakat, F. Helion, J.-L. Namy, J.-L. Vasse, and J. Szymoniak Organometallics 27 2008 4152 4157
48. N. Saino, F. Amemiya, E. Tanabe, K. Kase, and S. Okamoto Org. Lett. 8 2006 1439 1442