Pd-catalyzed ortho-arylation of N-aryloxazolidinones with simple arenes using sodium persulfate

Synlett

Volumn , Issue 7, 2011, Pages 974-978

  Yeung, Charles S ^a   Dong, Vy M ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

arylation; biaryl; cross coupling; metallacycle; palladium

Indexed keywords

CHEMICAL COMPOUND; N BIPHENYLARYLOXAZOLIDINONE DERIVATIVE; PERSULFATE SODIUM; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYST; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL STRUCTURE; HYDROGEN BOND; STOICHIOMETRY;

EID: 79954604106     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259731     Document Type: Article

References (45)

1. For a review of the therapeutic properties of N -aryloxazo-lidinones, see Halle E, Majcher-Peszynska J, Drewelow B, Chemother. J. 2002 11 1
2. Genin M J., Hutchinson D K., Allwine D A., Hester J B., Emmert D E., Garmon S A., Ford C W., Zurenko G E., Hamel J C., Schaadt R D., Stapert D, Yagi B H., Friis J M., Shobe E M., Adams W J., J. Med. Chem. 1998 41 5144
3. Tucker J A., Allwine D A., Grega K C., Barbachyn M R., Klock J L., Adamski J L., Brickner S J., Hutchinson D K., Ford C W., Zurenko G E., Conradi R A., Burton P S. M., J. Med. Chem. 1998 41 3727
4. Gleave D M., Brickner S J., Manninen P R., Allwine D A., Lovasz K D., Rohrer D C., Tucker J A., Zurenko G E., Ford C W., Bioorg. Med. Chem. Lett. 1998 8 1231
5. Moureau F, Wouters J, Vercauteren D P., Collin S, Evrard G, Durant F, Ducrey F, Koenig J J., Jarreau F X., Eur. J. Med. Chem. 1994 269
6. Moureau F, Wouters J, Vercauteren D P., Collin S, Evrard G, Durant F, Ducrey F, Koenig J J., Jarreau F X., Eur. J. Med. Chem. 1992 939
7. For selected examples, see:, Aroua L, Baklouti A, Synth. Commun. 2007 37 1935
8. Ghosh A, Sieser J E., Caron S, Couturier M, Dupont-Gaudet K, Girardin M, J. Org. Chem. 2006 71 1258
9. Griera R, Cantos-Llopart C, Amat M, Bosch J, de Castillo J.-C, Huguet J, Bioorg. Med. Chem. Lett. 2005 15 2515
10. Ghosh A, Sieser J E., Riou M, Cai W, Rivera-Ruiz L, Org. Lett. 2003 5 2207
11. Cacchi S, Fabrizi G, Goggiamani A, Heterocycles 2003 61 505
12. Gleave D M., Brickner S J., Manninen P R., Allwine D A., Lovasz K D., Rohrer D C., Tucker J A., Zurenko G E., Ford C W., Bioorg. Med. Chem. Lett. 1998 8 1231
13. Gleave D M., Brickner S J., J. Org. Chem. 1996 61 6470
14. For selected reviews, see:, Lyons T W., Sanford M S., Chem. Rev. 2010 110 1147
15. Colby D A., Bergman R G., Ellman J A., Chem. Rev. 2010 110 624
16. Daugulis O, Zaitsev V G., Shabashov D, Pham Q.-N, Lazareva A, Synlett 2006 3382
17. Ritleng V, Sirlin C, Pfeffer M, Chem. Rev. 2002 102 1731
18. Chen X, Engle K, Wang D.-H, Yu J.-Q, Angew. Chem. Int. Ed. 2009 48 5094
19. Dupont J, Consorti C S., Spencer J, Chem. Rev. 2005 105 2527
20. Shilov A E., Shul'pin G B., Chem. Rev. 1997 97 2879
21. Ryabov A D., Chem. Rev. 1990 90 403
22. Kalyani D, Deprez N R., Desai L V., Sanford M S., J. Am. Chem. Soc. 2005 127 7330
23. Wang D.-H, Hao X.-S, Wu D.-F, Yu J Q., Org. Lett. 2006 8 3387
24. Zhao X, Yeung C S., Dong V M., J. Am. Chem. Soc. 2010 132 5837
25. Bedford R B., Webster R L., Mitchell C J., Org. Biomol. Chem. 2009 7 4853
26. Xiao B, Fu Y, Xu J, Gong T.-J, Dai J.-J, Yi J, Liu L, J. Am. Chem. Soc. 2010 132 468
27. For selected reviews, see:, Corbet J.-P, Mignani G, Chem. Rev. 2006 106 2651
28. Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M, Chem. Rev. 2002 102 1359
29. For selected reviews, see
30. McGlacken G P., Batemann L M., Chem. Soc. Rev. 2009 38 2447
31. Ashenhurst J A., Chem. Soc. Rev. 2010 39 540
32. Li B.-J, Yang S.-D, Shi Z.-J, Synlett 2008 949
33. Ackermann L, Vicente R, Kapdi A, Angew. Chem. Int. Ed. 2009 48 9792
34. Stuart D R., Fagnou K, Science 2007 316 1172
35. Stuart D R., Villemure E, Fagnou K, J. Am. Chem. Soc. 2007 129 12072
36. Hull K L., Sanford M S., J. Am. Chem. Soc. 2007 129 11904
37. Hull K L., Sanford M S., J. Am. Chem. Soc. 2009 131 9651
38. Yeung C S., Zhao X, Borduas N, Dong V M., Chem. Sci. 2010 1 331
39. Li B.-J, Tian S.-L, Fang Z, Shi Z.-J, Angew. Chem. Int. Ed. 2008 47 1115
40. Brasche G, Garcia-Fortanet J, Buchwald S L., Org. Lett. 2008 10 2207
41. Xia J.-B, You S.-L, Organometallics 2007 26 4869
42. Cho S H., Hwang S J., Chang S, J. Am. Chem. Soc. 2008 130 9254
43. Dwight T A., Rue N R., Charyk D, Josselyn R, DeBoef B, Org. Lett. 2007 9 3137
44. Potavathri S, Dumas A S., Dwight T A., Naumiec G R., Hammann J M., DeBoef B, Tetrahedron Lett. 2008 49 4050
45. Li R, Jiang L, Lu W, Organometallics 2006 25 5973