Palladium-catalyzed synthesis of aryl ketones from carboxylic acids and arylboronic acids using EEDQ

Bulletin of the Korean Chemical Society

Volumn 31, Issue 9, 2010, Pages 2672-2674

  Kwon, Young Bum ^a   Choi, Bo Ram ^a   Lee, Seung Hwan ^a   Seo, Jin Soo ^a   Yoon, Cheol Min ^a  

^a Korea University   (South Korea)

Author keywords

Aryl ketone; Arylboronic acid; Carboxylic acid; EEDQ; Palladium

Indexed keywords

EID: 77957081687     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2010.31.9.2672     Document Type: Article

References (36)

1. (a) Dieter, R. K. Tetrahedron 1999, 55, 4177.
2. (b) Zhang, Y. D.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 15964.
3. (c) Hatano, B.; Kadokawa, J. I.; Tagaya, H. Tetrahedron Lett. 2002, 43, 5859.
4. (a) Shi, M.; Wu, L.; Lu, J.-M. Tetrahedron 2008, 64, 3315.
5. (b) Gmouh, S.; Yang, H.; Vaultier, M. Org. Lett. 2003, 5, 2219.
6. (c) Fillion, E.; Fishlock, D.; Wilsily, A.; Goll, J. M. J. Org. Chem. 2005, 70, 1316.
7. (d) Ruan, J.; Saidi, O.; Iggo, J. A.; Xiao, J. J. Am. Chem. Soc. 2008, 130, 10510. References cited therein.
8. (a) Labadie, J. W.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 669.
9. (b) Arisawa, M.; Torisawa, Y.; Kawahara, M.; Yamanaka, M.; Nishida, A.; Nakagawa, M. J. Org. Chem. 1997, 62, 4327.
10. (c) Wang, X.-J.; Zhang, L.; Sun, X.; Xu, Y.; Krishnamurthy, D.; Senanayake, C. H. Org. Lett. 2005, 7, 5593.
11. (d) Wang, D. H.; Zhang, Z. Z. Org. Lett. 2003, 5, 4645.
12. (a) Haddach, M.; McCarthy, J. R. Tetrahedron Lett. 1999, 40, 3109.
13. (b) Urawa, Y.; Ogura, K. Tetrahedron Lett. 2003, 44, 271.
14. (c) Bandgar, B. P.; Patil, A. V. Tetrahedron Lett. 2005, 46, 7627.
15. (d) Chen, H.; Deng, M. Z. Org. Lett. 2000, 2, 1649.
16. (e) Bumagin, N. A.; Korolev, D. N. Tetrahedron Lett. 1999, 40, 3057.
17. (a) Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260.
18. (b) Yu, Y.; Liebeskind, L. S. J. Org. Chem. 2004, 69, 3554.
19. Tatamidani, H.; Kakiuchi, F.; Chatani, N. Org. Lett. 2004, 6, 3597.
20. (a) Xin, B.; Zhang, Y.; Cheng, K. Synthesis 2007, 1970.
21. (b) Xin, B.; Zhang, Y.; Cheng, K. J. Org. Chem. 2006, 71, 5725.
22. (a) Gooßen, L. J.; Ghosh, K. Eur. J. Org. Chem. 2002, 19, 3254.
23. (b) Gooßen, L. J.; Ghosh, K. Chem. Commun. 2001, 2084.
24. (c) Gooßen, L. J.; Winkel, L.; Döhring, A.; Ghosh, K.; Paetzold, J. Synlett 2002, 1237.
25. (d) Gooßen, L. J.; Ghosh, K. Angew. Chem. Int. Ed. 2001, 40, 3458.
26. (a) Belleau, B.; Malek, G. J. Am. Chem. Soc. 1968, 90, 1651.
27. (b) Belleau, B.; Martel, R. R.; Lacasse, G.; Menard, M.; Weinberg, N. L.; Perron, Y. G. J. Am. Chem. Soc. 1968, 90, 823.
28. (c) Brown, J.; Williams, R. E. Can. J. Chem. 1971, 49, 3765.
29. Hyun, M. H.; Kang, M. H.; Han, S. C. Tetrahedron Lett. 1999, 40, 3435.
30. (a) Lee, J. H.; Kweon, J. S.; Yoon, C. M. Tetrahedron Lett. 2002, 43, 5771.
31. (b) Chang, Y. M.; Lee, S. H.; Nam, M. H.; Cho, M. Y.; Park, Y. S.; Yoon, C. M. Tetrahedron Lett. 2005, 46, 3053.
32. (c) Yamaoka, Y.; Miyabe, H.; Takemoto, Y. J. Am. Chem. Soc. 2007, 129, 6686.
33. Because DMF was identified to be better than acetonitrile in the reaction of 4-methoxybenzoic acid and methylbenzoic acid with phenylboronic acid, all the reactions were performed in DMF.
34. (a) Kakino, R.; Narahashi, H.; Shimizu, I.; Yamamoto, A. Chem. Lett. 2001, 1242.
35. (b) Kakino, R.; Narahashi, H.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2002, 75, 137.
36. (c) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314.