Palladium-catalyzed decarboxylative arylation of benzoylacrylic acids toward the synthesis of chalcones

Journal of Organic Chemistry

Volumn 78, Issue 10, 2013, Pages 5096-5102

  Unoh, Yuto ^a   Hirano, Koji ^a   Satoh, Tetsuya ^a,b   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL HALIDES; ARYLATIONS; ARYLBORONIC ACIDS; CHALCONE DERIVATIVES; CHALCONES; COPPER SALT; PALLADIUM-CATALYZED;

CATALYSIS;

AROMATIC COMPOUNDS;

ACRYLIC ACID DERIVATIVE; BORONIC ACID DERIVATIVE; CHALCONE DERIVATIVE; CINNAMIC ACID; COPPER; PALLADIUM;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; DECARBOXYLATION; ELECTRON TRANSPORT; ISOMER; SYNTHESIS;

ACRYLATES; BENZOATES; CATALYSIS; CHALCONES; DECARBOXYLATION; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM;

EID: 84878063406     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400716e     Document Type: Article

References (50)

1. de Meijere, A.; Diederich, F. Metal-Catalyzed Cross-Coupling Reactions; Wiley-VCH: Weinheim, Germany, 2004.
2. Tsuji, J. Palladium Reagents and Catalysts, 2 nd ed.; John Wiley & Sons: Chichester, U.K., 2004.
3. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002.
4. Cornella, J.; Larrosa, I. Synthesis 2012, 653
5. Rodriguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030
6. Weaver, V.; Recio, A., III; Grenning, A. J.; Tunge, J. A. Chem. Rev. 2011, 111, 1846
7. Satoh, T.; Miura, M. Synthesis 2010, 3395
8. Goossen, L. J.; Mamone, P.; Oppel, C. Adv. Synth. Catal. 2011, 353, 57
9. Mochida, S.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2011, 76, 3024
10. Cornella, J.; Righi, M.; Larrosa, I. Angew. Chem., Int. Ed. 2011, 50, 9429
11. Dai, J. J.; Liu, J.-H.; Luo, D.-F.; Liu, L. Chem. Commun. 2011, 47, 677
12. Zhao, H.; Wei, Y.; Xu, J.; Kan, J.; Su, W.; Hong, M. J. Org. Chem. 2011, 76, 882
13. Wang, C.; Rakshit, S.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 14006
14. Goossen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662
15. Bilodeau, F.; Brochu, M.-C.; Guimond, N.; Thesen, K. H.; Forgione, P. J. Org. Chem. 2010, 75, 1550
16. Zhang, F.; Greaney, M. F. Org. Lett. 2010, 12, 4745
17. Yamashita, M.; Hirano, K.; Satoh, T.; Miura, M. Chem. Lett. 2010, 39, 68
18. Wang, Z.; Ding, Q.; He, X.; Wu, J. Org. Biomol. Chem. 2009, 7, 863
19. For example, see: Moon, J.; Jang, M.; Lee, S. J. Org. Chem. 2009, 74, 1403
20. Collet, F.; Song, B.; Rudolphi, F.; Goossen, L. J. Eur. J. Org. Chem. 2011, 6486
21. Fang, P.; Li, M.; Ge, H. J. Am. Chem. Soc. 2010, 132, 11898
22. Itoh, M.; Hirano, K.; Satoh, T.; Shibata, Y.; Tanaka, K.; Miura, M. J. Org. Chem. 2013, 78, 1365
23. Yamashita, M.; Horiguchi, H.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2009, 74, 7481
24. Grealis, J. P.; Müller-Bunz, H.; Ortin, Y.; Casey, M.; McGlinchey, M. J. Eur. J. Org. Chem. 2013, 332
25. Juvale, K.; Pape, V. F. S.; Wiese, M. Bioorg. Med. Chem. 2012, 20, 346
26. Liu, M.; Wilairat, P.; Go, M.-L. J. Med. Chem. 2001, 44, 4443
27. Bianco, A.; Cavarischia, C.; Guiso, M. Eur. J. Org. Chem. 2004, 2894
28. Wu, X.-F.; Neumann, H.; Beller, M. Chem.-Asian J. 2012, 7, 282
29. Wu, X.-F.; Neumann, H.; Spannenberg, A.; Schulz, T.; Jiao, H.; Beller, M. J. Am. Chem. Soc. 2010, 132, 14596
30. Wu, X.-F.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 5284
31. Danko, M.; Andics, A.; Kosa, C.; Hrdlovic, P.; Vegh, D. Dyes Pigm. 2012, 92, 1257
32. Fodor, K.; Tomescova, V.; Köszegi, T.; Kron, I.; Perjési, P. Monatsh. Chem. 2011, 142, 463
33. Romanov, A. N.; Gularyan, S. K.; Polyak, B. M.; Sakovich, R. A.; Dobretsov, G. E.; Sarkisov, O. M. Phys. Chem. Chem. Phys. 2011, 13, 9518
34. Bakhshiev, N. G.; Gularyan, S. K.; Dobretsov, G. E.; Kirillova, A. Y.; Sarkisov, O. M.; Svetlichnyǐ, V. Y. Opt. Spectrosc. 2010, 109, 913
35. Chen, G.; Wang, H.-Y.; Liu, Y.; Xu, X.-P.; Ji, S.-J. Dyes Pigm. 2010, 85, 194
36. Bianchi, M.; Butti, A.; Christidis, Y.; Perronnet, J. F.; Barzaghi, R.; Cesana, A.; Nencioni, A. Eur. J. Med. Chem. 1988, 23, 45
37. Drakulic, B. J.; Stanojkovic, T. P.; Zizak, Z. S.; Dabovic, M. M. Eur. J. Med. Chem. 2011, 46, 3265
38. Jakubec, P.; Berkes, D.; Kolarovic, A.; Povazanec, F. Synthesis 2006, 4032
39. An, X.-L.; Chen, J.-R.; Li, C.-F.; Zhang, F.-G.; Zou, Y.-Q.; Guo, Y.-C.; Xiao, W.-J. Chem.-Asian J. 2010, 5, 2258
40. Syam, S.; Abdelwahab, S. I.; Al-Mamary, M. A.; Mohan, S. Molecules 2012, 17, 6179
41. Braun, R. U.; Ansorge, M.; Müller, T. J. J. Chem.-Eur. J. 2006, 12, 9081
42. Matthias, C.; Kuck, D. Int. J. Mass Spectrom. 2002, 217, 131
43. Stroba, A.; Schaeffer, F.; Hindie, V.; Lopez-Garcia, L.; Adrian, I.; Frhner, W.; Hartmann, R. W.; Biondi, R. M.; Engel, M. J. Med. Chem. 2009, 52, 4683
44. Varga, S.; Jakab, G.; Drahos, L.; Holczbauer, T.; Czugler, M.; Soos, T. Org. Lett. 2011, 13, 5416
45. Silver, N. L.; Boykin, D. W. J. Org. Chem. 1970, 35, 759
46. Fang, F.; Li, Y.; Tian, S.-K. Eur. J. Org. Chem. 2011, 1084
47. Batovska, D.; Parusheva, S.; Slavova, A.; Bankova, V.; Tsvetkova, I.; Ninova, M.; Najdenski, H. Eur. J. Med. Chem. 2007, 42, 87
48. Ono, M.; Watanabe, R.; Kawashima, H.; Cheng, Y.; Kimura, H.; Watanabe, H.; Haratake, M.; Saji, H.; Nakayama, M. J. Med. Chem. 2009, 52, 6394
49. Elias, G.; Rao, M. N. A. Eur. J. Med. Chem. 1988, 23, 379
50. Meier, H.; Aust, H.; Ickenroth, D.; Kolshorn, H. J. Prakt. Chem. (Weinheim, Ger.) 1999, 341, 529