Palladium-catalyzed direct arylation of 4-hydroxycoumarins with arylboronic acids via C-OH bond activation

Tetrahedron Letters

Volumn 50, Issue 18, 2009, Pages 2103-2105

  Luo, Yong ^a   Wu, Jie ^a,b  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

4 Hydroxycoumarin; Arylboronic acid; C OH bond activation; Palladium chloride

Indexed keywords

4 ARYLCOUMARIN DERIVATIVE; 4 HYDROXYCOUMARIN DERIVATIVE; ARYLBORONIC ACID DERIVATIVE; BORONIC ACID DERIVATIVE; CARBON; COUMARIN DERIVATIVE; HYDROGEN; OXYGEN; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL BOND; DRUG STRUCTURE; DRUG SYNTHESIS; QUANTITATIVE ANALYSIS;

EID: 62349111892     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.02.116     Document Type: Article

References (72)

1. Tsuji J. Palladium Reagents and Catalysts. 2nd ed. (2004), John Wiley & Sons, Chichester, UK
2. de Meijere A., and Diederich F. Metal-Catalyzed Cross-Coupling Reactions. 2nd ed. (2004), John Wiley & Sons, Weinheim, Germany
3. Kang F.-A., Sui Z., and Murray W.V. J. Am. Chem. Soc. 130 (2008) 11300
4. Ackermann L., and Mulzer M. Org. Lett. 10 (2008) 5043
5. Zhang L., and Wu J. J. Am. Chem. Soc. 130 (2008) 12250
6. Zhang L., Qing J., Yang P., and Wu J. Org. Lett. 10 (2008) 4971
7. Zhang L., and Wu J. Adv. Synth. Catal. 350 (2008) 2409
8. Wang Z., Fan R., and Wu J. Adv. Synth. Catal. 349 (2007) 1943
9. Zhang L., Meng T., and Wu J. J. Org. Chem. 72 (2007) 9346
10. Zhang L., Meng T., Fan R., and Wu J. J. Org. Chem. 72 (2007) 7279
11. Wang Z., Wang B., and Wu J. J. Comb. Chem. 9 (2007) 811
12. For selected examples, see:. Gao K., and Wu J. Org. Lett. 10 (2008) 2251
13. Ding Q., and Wu J. Adv. Synth. Catal. 350 (2008) 1850
14. Ding Q., and Wu J. J. Comb. Chem. 10 (2008) 541
15. Ding Q., and Wu J. Org. Lett. 9 (2007) 4959
16. Zhang L., and Wu J. Adv. Synth. Catal. 349 (2007) 1047
17. Gao K., and Wu J. J. Org. Chem. 72 (2007) 8611
18. Ding Q., Ye Y., Fan R., and Wu J. J. Org. Chem. 72 (2007) 5439
19. Sun W., Ding Q., Sun X., Fan R., and Wu J. J. Comb. Chem. 9 (2007) 690
20. For selected examples, see. Murakami A., Gao G., Omura M., Yano M., Ito C., Furukawa H., Takahashi D., Koshimizu K., and Ohigashi H. Bioorg. Med. Chem. Lett. 10 (2000) 59
21. Maier W., Schmidt J., Nimtz M., Wray V., and Strack D. Phytochemistry 54 (2000) 473
22. Garcia-Argaez A.N., Ramirez Apan T.O., Delgado H.P., Velazquez G., and Martinez-Vazquez M. Planta Med. 66 (2000) 279
23. Zhou P., Takaishi Y., Duan H., Chen B., Honda G., Itoh M., Takeda Y., Kodzhimatov O.K., and Lee K.-H. Phytochemistry 53 (2000) 689
24. Khalmuradov M.A., and Saidkhodzhaev A.I. Chem. Nat. Compd. 35 (1999) 364
25. Kamalam M., and Jegadeesan M. Indian Drugs 36 (1999) 484
26. Tan R.X., Lu H., Wolfender J.L., Yu T.T., Zheng W.F., Yang L., Gafner S., and Hostettmann K. Planta Med. 65 (1999) 64
27. Bal-Tembe S., Joshi D.D., and Lakdawala A.D. Indian J. Chem., Sect. B: Org. Chem. Include. Med. Chem. 35B (1996) 518
28. Silvan A.M., Abad M.J., Bermejo P., Villar A., and Sollhuber M. J. Nat. Prod. 59 (1996) 1183
29. Yang Y.M., Hyun J.W., Sung M.S., Chung H.S., Kim B.K., Paik W.H., Kang S.S., and Park J.G. Planta Med. 62 (1996) 353
30. For selected examples, see:. Gellert M., O'Dea M.H., Itoh T., and Tomizawa J.I. Proc. Natl. Acad. Sci. U.S.A 73 (1976) 4474-4478
31. Murray R.D.H., Méndez J., and Brown S.A. The Natural Coumarins: Occurrence, Chemistry, and Biochemistry (1982), Wiley, New York
32. Ali J.A., Jackson A.P., Howells A.J., and Maxwell A. Biochemistry 32 (1993) 2717
33. Pereira N.A., Pereira B.M.R., Celia do Nascimento M., Parente J.P., and Mors W.B. Planta Med 60 (1994) 99
34. Vlietinck A.J., De Bruyne T., Apers S., and Pieters L.A. Planta Med. 64 (1998) 97
35. Murakami A., Gao G., Omura M., Yano M., Ito C., Furukawa H., Takahashi D., Koshimizu K., and Ohigashi H. Bioorg. Med. Chem. Lett. 10 (2000) 59
36. Xia Y., Yang Z.-Y., Xia P., Hackl T., Hamel E., Mauger A., Wu J.-H., and Lee K.-H. J. Med. Chem. 44 (2001) 3932
37. Chen Y.-L., Fang K.-C., Sheu J.-Y., Hsu S.-L., and Tzeng C.-C. J. Med. Chem. 44 (2001) 2374
38. Yamaguchi T., Fukuda T., Ishibashi F., and Iwao M. Tetrahedron Lett. 47 (2006) 3755 and references cited therein
39. For selected examples, see:. von Pechmann H., and Duisberg C. Chem. Ber. 17 (1884) 929
40. Johnson J.R. Org. React. 1 (1942) 210
41. Jones G. Org. React. 15 (1967) 204
42. Brufola G., Fringuelli F., Piermatti O., and Pizzo F. Heterocycles 43 (1996) 1257
43. Shirner R.L. Org. React. 1 (1942) 1
44. Narasimhan N.S., Mali R.S., and Barve M.V. Synthesis (1979) 906
45. Yavari I., Hekmat-Shoar R., and Zonouzi A. Tetrahedron Lett. 39 (1998) 2391
46. Cartwright G.A., and McNab W. J. Chem. Res. (S) (1997) 296
47. Alexander V.M., Bhat R.P., and Samant S.D. Tetrahedron Lett. 46 (2005) 6957 and references cited therein
48. Sengh V., Sengh J., Kaur K.P., and Kad G.L. J. Chem. Res. (S) (1997) 58
49. Frere S., Thiery V., and Besson T. Tetrahedron Lett. 42 (2001) 2791
50. John E.V.O., and Israelstam S.S. J. Org. Chem. 26 (1961) 240
51. Hoefnagel A.J., Gennewagh E.A., Downing R.S., and Bekkum H.V. J. Chem. Soc., Chem. Commun. (1995) 225
52. Wu J., Diao T.-N., Sun W., and Li Y. Synth. Commun. 36 (2006) 2949
53. Sharma G.V.M., Reddy J.J., Lakshmi P.S., and Krishna P.R. Tetrahedron Lett. 46 (2005) 6119
54. For examples, see:. Tang Z.Y., and Hu Q.-S. Adv. Synth. Catal. 346 (2004) 1635
55. Wu J., Liao Y., and Yang Z. J. Org. Chem. 66 (2001) 3642
56. Lei J.-G., Xu M.-H., and Lin G.-Q. Synlett (2004) 2364
57. Wu J., Wang L., Fathi R., and Yang Z. Tetrahedron Lett. 43 (2002) 4395
58. Schio L., Chatreaux F., and Klich M. Tetrahedron Lett. 41 (2000) 1543
59. Yao M.-L., and Deng M.-Z. Hetero. Chem. 11 (2000) 380
60. Wu J., and Yang Z. J. Org. Chem. 66 (2001) 7875
61. Wu J., Zhang L., and Gao K. Eur. J. Org. Chem. (2006) 5260
62. Wu J., and Wang X. Org. Biomol. Chem. 4 (2006) 1348
63. Wu J., Zhang L., and Xia H.-G. Tetrahedron Lett. 47 (2006) 1525
64. Wu J., Zhang L., and Luo Y. Tetrahedron Lett. 47 (2006) 6747
65. Shi Z., and He C. J. Org. Chem. 69 (2004) 3669 and references cited therein
66. Jia C.G., Piao D.G., Oyamada J.Z., Lu W.J., Kitamura T., and Fujiwara Y. Science 287 (2000) 1992
67. Fürstner A., and Mamane V. J. Org. Chem. 67 (2002) 6264
68. Pastine S.J., Youn S.W., and Sames D. Org. Lett. 5 (2003) 1055
69. Youn S.W., Pastine S.J., and Sames D. Org. Lett. 6 (2004) 581
70. Wu, J.; Yang, Z.; Fathi, R.; Zhu, Q.; Wang, L. US Patent 6 703 514, 2004.
71. Wu, J.; Yang, Z.; Fathi, R.; Zhu, Q. US Patent 7 148 253, 2006.
72. ++1): 223.