Palladium-catalyzed Suzuki-Miyaura couplings of potassium aryl trifluoroborates with 4-tosyloxycoumarins or 4-tosyloxyquinolin-2(1H)-one

Tetrahedron Letters

Volumn 47, Issue 10, 2006, Pages 1525-1528

  Wu, Jie ^a,b   Zhang, Liang ^a   Xia, Hong Guang ^a  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

4 Tosyloxycoumarins; 4 Tosyloxyquinolin 2(1H) one; Palladium catalyst; Potassium aryl trifluoroborates; Suzuki Miyaura couplings

Indexed keywords

4 TOSYLOXYCOUMARIN; 4 TOSYLOXYQUINOLIN 2 ONE; BORINIC ACID DERIVATIVE; COUMARIN DERIVATIVE; PALLADIUM; POTASSIUM ARYL TRIFLUOROBORATE; POTASSIUM DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; SUZUKI REACTION;

EID: 31944444620     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.01.020     Document Type: Article

References (48)

1. Recent reviews: N. Miyaura Top. Curr. Chem. 219 2002 11 59
2. J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, and M. Lemaire Chem. Rev. 102 2002 1359 1469
3. S. Kotha, K. Lahiri, and D. Kashinath Tetrahedron 58 2002 9633 9695
4. T. Onak Organoborane Chemistry 1975 Academic Press New York
5. E. Vedejs, R.W. Chapman, S.C. Fields, S. Lin, and M.R. Schrimpf J. Org. Chem. 60 1995 3020 3027
6. E. Vedejs, S.C. Fields, R. Hayashi, S.R. Hitchcock, D.R. Powell, and M.R. Schrimpf J. Am. Chem. Soc. 121 1999 2460 2470
7. R.A. Batey, and T.D. Quach Tetrahedron Lett. 42 2001 9099 9103
8. G.A. Molander, and B. Biolatto Org. Lett. 4 2002 1867 1870
9. G.A. Molander, and B. Biolatto J. Org. Chem. 68 2003 4302 4314
10. T.E. Barder, and S.L. Buchwald Org. Lett. 6 2004 2649 2652 and references cited therein
11. S. Darses, and J.-P. Genet Eur. J. Org. Chem. 2003 4313 4327
12. G.A. Molander, and R. Figuroa Aldrichim. Acta 38 2005 49 56
13. S. Darses, J.-L. Brayer, J.-P. Demoute, and J.-P. Genet Tetrahedron Lett. 38 1997 4393 4396
14. S. Darses, G. Michaud, and J.-P. Genet Eur. J. Org. Chem. 1999 1875 1883
15. M. Xia, and Z.-C. Chen J. Chem. Res. (S) 1999 400 401
16. G.A. Molander, and L.A. Felix J. Org. Chem. 70 2005 3950 3956
17. G.W. Kabalka, and M. Al-Masum Tetrahedron Lett. 46 2005 6329 6331
18. G.A. Molander, B.W. Katona, and F. Machrouhl J. Org. Chem. 67 2002 8416 8423
19. G.-H. Fang, Z.-J. Yan, and M.-Z. Deng Org. Lett. 6 2004 357 360
20. For Suzuki-Miyaura reaction, see: Z.-Y. Tang, and Q.-S. Hu J. Am. Chem. Soc. 126 2004 3058 3059
21. H.N. Nguyen, X. Huang, and S.L. Buchwald J. Am. Chem. Soc. 125 2003 11818 11819
22. V. Percec, J.-Y. Bae, and D.H. Hill J. Org. Chem. 60 1995 1060 1065
23. Y. Kobayashi, and R. Mizojiri Tetrahedron Lett. 37 1996 8531 8534
24. D. Zim, V.R. Lando, J. Dupont, and A.L. Monteiro Org. Lett. 3 2001 3049 3051
25. M.K. Lakshman, P.F. Thomson, M.A. Nuqui, J.H. Hilmer, N. Sevova, and B. Boggess Org. Lett. 4 2002 1479 1482
26. M.A. Huffman, and N. Yasuda Synlett 1999 471 473
27. J. Wu, L. Wang, R. Fathi, and Z. Yang Tetrahedron Lett. 43 2002 4395 4397
28. J. Wu, Q. Zhu, L. Wang, R. Fathi, and Z. Yang J. Org. Chem. 68 2003 670 673
29. V. Percec, G.M. Golding, J. Smidrkal, and O. Weichold J. Org. Chem. 69 2004 3447 3452
30. J.M. Baxter, D. Steinhuebel, M. Palucki, and I.W. Davies Org. Lett. 7 2005 215 218
31. Z.Y. Tang, and Q.-S. Hu Adv. Synth. Catal. 346 2004 1635 1637
32. During our manuscript reviewing, Steinhuebel and Baxter reported an example of Pd-catalyzed couplings of tosylates with aryl trifluoroborates: D. Steinhuebel, J.M. Baxter, M. Palucki, and I.W. Davies J. Org. Chem. 70 2005 10124 10127
33. Alkyne coupling: X. Fu, S. Zhang, J. Yin, and D.P. Schumacher Tetrahedron Lett. 43 2002 6673 6676
34. J. Wu, Y. Liao, and Z. Yang J. Org. Chem. 66 2001 3642 3645
35. Heck coupling: X. Fu, S. Zhang, J. Yin, T.L. McAllister, S.A. Jiang, C.-H. Tann, T.K. Thiruvengadam, and F. Zhang Tetrahedron Lett. 43 2002 573 576
36. Kumada coupling: A.H. Roy, and J.F. Hartwig J. Am. Chem. Soc. 125 2003 8704 8705
37. Iron-catalyzed coupling of alkyl Grignard reagents with ArOTs: A. Fürstner, A. Leitner, M. Méndez, and H. Krause J. Am. Chem. Soc. 124 2002 13856 13863
38. Stille couplings of aryl arenesulfonates: D. Badone, R. Cecchi, and U. Guzzi J. Org. Chem. 57 1992 6321 6323
39. F. Nagatsugi, K. Uemura, S. Nakashima, M. Minoru, and S. Sasaki Tetrahedron Lett. 36 1995 421 424
40. L. Schio, F. Chatreaux, and M. Klich Tetrahedron Lett. 41 2000 1543 1547
41. Palladium-catalyzed Negishi-type reaction of arenesulfonates: J. Wu, Y. Liao, and Z. Yang J. Org. Chem. 66 2001 3642 3645
42. 3/Zn/toluene system, please see: J.-G. Lei, M.-H. Xu, and G.-Q. Lin Synlett 2004 2364 2368
43. B.R. Stockwell, S.J. Haggarty, and S.L. Schreiber Chem. Biol. 6 1999 71 83
44. T.U. Mayer, T.M. Kapoor, S.J. Haggarty, R.W. King, S.L. Schreiber, and T.J. Mitchison Science 286 1999 971 974
45. Y. Liao, Y. Hu, J. Wu, Q. Zhu, M. Donovan, R. Fathi, and Z. Yang Curr. Med. Chem. 10 2003 2285 2316
46. J. Wu, L. Zhang, and X. Sun Chem. Lett. 34 2005 550 551
47. J. Wu, L. Zhang, and T.-N. Diao Synlett 2005 2653 2657
48. M.-L. Yao, and M.-Z. Deng Heterocycl. Chem. 11 2000 380 382