Iron-catalyzed oxidative cross-coupling of phenols and alkenes

Organic Letters

Volumn 15, Issue 12, 2013, Pages 3174-3177

  Kshirsagar, Umesh A ^a   Regev, Clil ^a   Parnes, Regev ^a   Pappo, Doron ^a  

^a BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

1,1'-BI-2-NAPHTHOL; 2,2' DIHYDROXY 1,1' BINAPHTHYL; ALKENE; IRON; NAPHTHOL DERIVATIVE; PHENOL DERIVATIVE; STYRENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; OXIDATIVE COUPLING;

ALKENES; CATALYSIS; IRON; MOLECULAR STRUCTURE; NAPHTHOLS; OXIDATION-REDUCTION; OXIDATIVE COUPLING; PHENOLS; STYRENES;

EID: 84879395307     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol401532a     Document Type: Article

References (47)

1. Quideau, S.; Deffieux, D.; Douat-Casassus, C.; Pouysegu, L. Angew. Chem., Int. Ed. 2011, 50, 586
2. Riviere, C.; Pawlus, A. D.; Merillon, J. M. Nat. Prod. Rep. 2012, 29, 1317
3. Wink, M. Phytochemistry 2003, 64, 3
4. Chong, J.; Poutaraud, A.; Hugueney, P. Plant Science 2009, 177, 143
5. S Velu, S.; F Thomas, N.; F Weber, J.-F. Curr. Org. Chem. 2012, 16, 605
6. Sako, M.; Hosokawa, H.; Ito, T.; Iinuma, M. J. Org. Chem. 2004, 69, 2598
7. Bruschi, M.; Orlandi, M.; Rindone, B.; Rummakko, P.; Zoia, L. J. Phys. Org. Chem. 2006, 19, 592
8. Takaya, Y.; Terashima, K.; Ito, J.; He, Y.-H.; Tateoka, M.; Yamaguchi, N.; Niwa, M. Tetrahedron 2005, 61, 10285
9. Chen, P.-Y.; Wu, Y.-H.; Hsu, M.-H.; Wang, T.-P.; Wang, E.-C. Tetrahedron 2013, 69, 653
10. Wang, G.-W.; Wang, H.-L.; Capretto, D. A.; Han, Q.; Hu, R.-B.; Yang, S.-D. Tetrahedron 2012, 68, 5216
11. Snyder, S. A.; Kontes, F. J. Am. Chem. Soc. 2009, 131, 1745
12. Li, C.; Lu, J.; Xu, X.; Hu, R.; Pan, Y. Green Chem. 2012, 14, 3281
13. Navarra, C.; Goodwin, C.; Burton, S.; Danieli, B.; Riva, S. J. Mol. Catal. B: Enzym. 2010, 65, 52
14. Syrjänen, K.; Brunow, G. Tetrahedron 2001, 57, 365
15. Moeller, K. D. Tetrahedron 2000, 56, 9527
16. Kerns, M. L.; Conroy, S. M.; Swenton, J. S. Tetrahedron Lett. 1994, 35, 7529
17. Gates, B. D.; Dalidowicz, P.; Tebben, A.; Wang, S.; Swenton, J. S. J. Org. Chem. 1992, 57, 2135
18. Kim, S.; Noda, S.; Hayashi, K.; Chiba, K. Org. Lett. 2008, 10, 1827
19. Kim, S.; Hirose, K.; Uematsu, J.; Mikami, Y.; Chiba, K. Chem.-Eur. J. 2012, 18, 6284
20. Chiba, K.; Fukuda, M.; Kim, S.; Kitano, Y.; Tada, M. J. Org. Chem. 1999, 64, 7654
21. Roupe, K. A.; Remsberg, C. M.; Yanez, J. A.; Davies, N. M. Curr. Clin. Pharmacol. 2006, 1, 81
22. Dohi, T.; Hu, Y.; Kamitanaka, T.; Kita, Y. Tetrahedron 2012, 68, 8424
23. Chen, D. Y.; Youn, S. W. Chem.-Eur. J. 2012, 18, 9452
24. Wang, D.-H.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 5767
25. Wang, X.; Lu, Y.; Dai, H.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 12203
26. Rousseaux, S.; Davi, M.; Sofack-Kreutzer, J.; Pierre, C.; Kefalidis, C. E.; Clot, E.; Fagnou, K.; Baudoin, O. J. Am. Chem. Soc. 2010, 132, 10706
27. Lafrance, M.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 14570
28. Zhang, H.; Ferreira, E. M.; Stoltz, B. M. Angew. Chem., Int. Ed. 2004, 43, 6144
29. Snyder, S. A.; Gollner, A.; Chiriac, M. I. Nature 2011, 474, 461
30. Sun, A. Y.; Simonyi, A.; Sun, G. Y. Free Radical Biol. Med. 2002, 32, 314
31. Direct, C. Chem. Rev. 2011, 111, 1293
32. Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780
33. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
34. Ashenhurst, J. A. Chem. Soc. Rev. 2010, 39, 540
35. DeMartino, M. P.; Chen, K.; Baran, P. S. J. Am. Chem. Soc. 2008, 130, 11546
36. Richter, J. M.; Whitefield, B. W.; Maimone, T. J.; Lin, D. W.; Castroviejo, M. P.; Baran, P. S. J. Am. Chem. Soc. 2007, 129, 12857
37. Baran, P. S.; Richter, J. M. J. Am. Chem. Soc. 2004, 126, 7450
38. Li, C.-J. Acc. Chem. Res. 2008, 42, 335
39. Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2004, 126, 11810
40. Guo, X.; Yu, R.; Li, H.; Li, Z. J. Am. Chem. Soc. 2009, 131, 17387
41. Parnes, R.; Kshirsagar, U. A.; Werbeloff, A.; Regev, C.; Pappo, D. Org. Lett. 2012, 14, 3324
42. Kshirsagar, U. A.; Parnes, R.; Goldshtein, H.; Ofir, R.; Zarivach, R.; Pappo, D. Chem.-Eur. J. 2013, 10.1002/chem.201300389
43. Oguma, T.; Katsuki, T. J. Am. Chem. Soc. 2012, 134, 20017
44. Rudolph, A.; Bos, P. H.; Meetsma, A.; Minnaard, A. J.; Feringa, B. L. Angew. Chem., Int. Ed. 2011, 50, 5834
45. Zhuo, C.-X.; Zhang, W.; You, S.-L. Angew. Chem., Int. Ed. 2012, 51, 12662
46. Sue, D.; Kawabata, T.; Sasamori, T.; Tokitoh, N.; Tsubaki, K. Org. Lett. 2009, 12, 256
47. Schädel, U.; Habicher, W. D. Heterocycles 2002, 57, 1049