Palladium-catalyzed cross-coupling reaction of resin-bound chlorotriazines

Tetrahedron Letters

Volumn 44, Issue 32, 2003, Pages 6141-6144

  Bork, Jacqueline T ^a   Lee, Jae Wook ^a   Chang, Young Tae ^a  

^a NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; DIOXANE DERIVATIVE; PALLADIUM; RESIN; TRIAZINE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE;

LATEOLABRAX JAPONICUS;

EID: 0038644076     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01451-5     Document Type: Article

References (40)

1. Bringmann G., Pokorny F. Cordell G.A. The Alkaloids. 46:1995;127 Academic Press, New York.
2. Furukawa H., Wu T.S., Ohta T. Chem. Pharm. Bull. 31:1983;4202-4205.
3. Bringmann G., Günther C., Ochse M., Schupp O., Tasler S. Prog. Chem. Org. Nat. Prod. 82:2001;1-293.
4. Gallant M., Carriére M.C., Chateauneuf A., Denis D., Gareau Y., Godbout C., Greig G., Juteau H., Lachance N., Lacombe P., Lamontagne S., Metters K.M., Rochette C., Ruel R., Slipetz D., Sawyer N., Tremblay N., Labelle M. Biorg. Med. Chem. Lett. 12:2002;2583-2586.
5. Sasaki S., Cho N., Nara Y., Harada M., Endo S., Suzuki N., Furuya S., Fujino M. J. Med. Chem. 46:2003;113-124.
6. Hotzel A., Schmid D.G., Nicholson G.J., Graeme J., Stevanovic S., Schimana J., Gebhardt K., Fiedler H.S., Jung G. J. Antibio. 55:2002;571-577.
7. Ikegaya, K.; Ozaki, M.; Kawashima, T.; Miura, I.; Muramatsu, N. Preparation of biarylalkylenecarbamic acid derivatives as agricultural and horticultural fungicides. PCT Int. Appl., WO9910317; 1999. Hatanaka, Y.; Hagiwara, E.; Gouda, K.; Hiyama, T. Process of producing unsaturated organic compounds such as biaryls or arylpyridine derivative by coupling of organohalosilane with halobenzenes or halopyridines. PCT Int. Appl. WO9628401; 1996.
8. Bringmann G., Stowasser R., Goebel L. J. Organomet. Chem. 544:1997;7-13.
9. Lee D.H., Im J.H., Lee J.H., Hong J.I. Tetrahedron Lett. 43:2002;9637-9640.
10. Messner M., Kozhushkov S., De Meijere A. Eur. J. Org. Chem. 2000;1137-1155.
11. Larock R.C. Comprehensive Organic Transformations. 2nd ed: 1999;362-364 Wiley-VCH, New York.
12. Miyaura N., Suzuki A. Chem. Rev. 95:1995;2457-2483.
13. Hassan J., Sévignon M., Gozzi C., Schulz E., Lemaire M. Chem. Rev. 102:2002;1359-1469.
14. Littke A.F., Fu G.C. Angew. Chem., Int. Ed. 41:2002;4176-4211.
15. Littke A.F., Fu G.C. Angew. Chem., Int. Ed. 37:1998;3387-3388.
16. Littke A.F., Dai C., Fu G.C. J. Am. Chem. Soc. 122:2000;4020-4028.
17. Yin J., Buchwald S.L. J. Am. Chem. Soc. 122:2000;12051-12052.
18. Yin J., Rainka M.P., Zhang X.-X., Buchwald S.L. J. Am. Chem. Soc. 124:2002;1162-1163.
19. Schomaker J.M., Delia T.J. J. Org. Chem. 66:2001;7125-7128.
20. Cooke G., de Cremiers A., Rotello V.M., Tarbit B., Vanderstraeten P.E. Tetrahedron. 57:2001;2787-2789.
21. Ishikura M., Kamada M., Terashima M. Synthesis. 1984;936-938.
22. Mitchell M.B., Wallbank P.J. Tetrahedron Lett. 32:1991;2273-2276.
23. Ali N.M., McKillop A., Mitchell M.B., Rebelo R.A., Wallbank P.J. Tetrahedron. 48:1992;8117-8126.
24. Zhang H., Chan K.S. Tetrahedron Lett. 37:1996;1043-1044.
25. Zhang H., Kwong F.Y., Tian Y., Chan K.S. J. Org. Chem. 63:1998;6886-6890.
26. Havelková M., Hocek M., Cesnek M., Dvorák D. Synlett. 1999;1145-1147.
27. Ding S., Gray N.S., Ding Q., Schultz P.G. Tetrahedron Lett. 42:2001;8751-8755.
28. Havelková M., Dvorák D., Hocek M. Synthesis. 11:2001;1704-1710.
29. Janietz D., Bauer M. Synthesis. 1:1993;33-34.
30. Cocuzza A.J., Chidester D.R., Culp S., Fitzgerald P., Gilligan P. Bioorg. Med. Chem. Lett. 9:1999;1063-1066.
31. Wade J., Krueger C.A. J. Comb. Chem. 5:2003;267-272.
32. Ding S., Gray N.S., Wu X., Ding Q., Schultz P.G. J. Am. Chem. Soc. 124:2002;1594-1596.
33. Brun V., Legraverend M., Grierson D.S. Tetrahedron. 58:2002;7911-7923.
34. Moon H.S., Jacobson E., Khersonsky S.M., Luzung M., Walsh D., Xiong W., Lee J.W., Parikh P., Lam J.C., Kang T.W., Rosania G.F., Schier A., Chang Y.T. J. Am. Chem. Soc. 124:2002;11608-11609.
35. Bork J.T., Lee J.W., Khersonsky S.M., Moon H.S., Chang Y.T. Org. Lett. 5:2003;117-120.
36. Zhang C., Haung J., Trudell M.L., Nolan S.P. J. Org. Chem. 64:1999;3804-3805 Arduengo, A. J., III, US patent 5 077 414; 1991.
37. Arduengo A.J. III, Dias H.V.R., Harlow R.L., Kline M. J. Am. Chem. Soc. 114:1992;5530-5534.
38. Haung J., Grasa G., Nolan S.P. Org. Lett. 1:1999;1307-1309.
39. Old D.W., Harris M.C., Buchwald S.L. Org. Lett. 2:2000;1403-1406.
40. 3) δ 3.96 (s, 3H), 4.49 (s, 2H), 4.69 (m, 2H, J=5.76 Hz), 5.7 (br, 1H), 6.89 (d, 2H, J=7.45 Hz), 7.26-7.38 (m, 5H), 7.38-7.56 (m, 5H), 8.37-8.54 (m, 2H).