Oxidative alkenylation of aromatic esters by ruthenium-catalyzed twofold C-H bond cleavages

Organic Letters

Volumn 14, Issue 16, 2012, Pages 4110-4113

  Graczyk, Karolina ^a   Ma, Wenbo ^a   Ackermann, Lutz ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; ESTER; ORGANOMETALLIC COMPOUND; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

ALKYNES; CATALYSIS; ESTERS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; RUTHENIUM; STEREOISOMERISM;

EID: 84865268124     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301759v     Document Type: Article

References (58)

1. Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215-1292
2. Wencel-Delord, J.; Dröge, T.; Liu, F.; Glorius, F. Chem. Soc. Rev. 2011, 40, 4740-4761
3. Ackermann, L.; Potukuchi, H. K. Org. Biomol. Chem. 2010, 8, 4503-4513
4. Daugulis, O. Top. Curr. Chem. 2010, 292, 57-84
5. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677-685
6. Lapointe, D.; Fagnou, K. Chem. Lett. 2010, 39, 1119-1126
7. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624-655
8. Boutadla, Y.; Davies, D. L.; Macgregor, S. A.; Poblador-Bahamonde, A. I. Dalton Trans. 2009, 5820-5831
9. Ackermann, L.; Vicente, R; Kapdi, A. Angew. Chem., Int. Ed. 2009, 48, 9792-9826 and references cited therein
10. Moritani, I.; Fujiwara, Y. Tetrahedron Lett. 1967, 8, 1119-1122
11. Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633-639
12. Matsumoto, T.; Yoshida, H. Chem. Lett. 2000, 29, 1064-1065
13. Matsumoto, T.; Periana, R. A.; Taube, D. J.; Yoshida, H. J. Catal. 2002, 206, 272-280
14. Baxter, R. D.; Sale, D.; Engle, K. M.; Yu, J.-Q.; Blackmond, D. G. J. Am. Chem. Soc. 2012, 134, 4600-4606
15. Patureau, F. W.; Nimphius, C.; Glorius, F. Org. Lett. 2011, 13, 6346-6349
16. Rakshit, S.; Grohmann, C.; Besset, T.; Glorius, F. J. Am. Chem. Soc. 2011, 133, 2350-2353
17. Patureau, F. W.; Besset, T.; Glorius, F. Angew. Chem., Int. Ed. 2011, 50, 1064-1067
18. Mochida, S.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2011, 76, 3024-3033
19. Li, X.; Gong, X.; Zhao, M.; Song, G.; Deng, J.; Li, X. Org. Lett. 2011, 13, 5808-5811
20. Patureau, F. W.; Glorius, F. J. Am. Chem. Soc. 2010, 132, 9982-9983
21. Lu, Y.; Wang, D.-H.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 5916-5921
22. Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2007, 1407-1409
23. Dams, M.; De Vos, D. E.; Celen, S.; Jacobs, P. A. Angew. Chem., Int. Ed. 2003, 42, 3512-3515
24. Boele, M. D. K.; van Strijdonck, G. P. F.; de Vries, A. H. M.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2002, 124, 1586-1587
25. Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2012, 45, 788-802
26. Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651-3678
27. Satoh, T.; Miura, M. Chem.-Eur. J. 2010, 16, 11212-11222 and references cited therein
28. Hashimoto, Y.; Ortloff, T.; Hirano, K.; Satoh, T.; Bolm, C.; Miura, M. Chem. Lett. 2012, 41, 151-153
29. Li, B.; Ma, J.; Wang, N.; Feng, H.; Xu, S.; Wang, B. Org. Lett. 2012, 14, 736-739
30. Ackermann, L.; Wang, L.; Wolfram, R.; Lygin, A. V. Org. Lett. 2012, 14, 728-731
31. Hashimoto, Y.; Ueyama, T.; Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M. Chem. Lett. 2011, 40, 1165-1166
32. Arockiam, P. B.; Fischmeister, C.; Bruneau, C.; Dixneuf, P. H. Green Chem. 2011, 13, 3075-3078
33. Ackermann, L.; Pospech, J. Org. Lett. 2011, 13, 4153-4155
34. Ueyama, T.; Mochida, S.; Fukutani, T.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2011, 13, 706-708
35. Kwon, K.-H.; Lee, D. W.; Yi, C. S. Organometallics 2010, 29, 5748-5750 and references cited therein
36. Weissman, H.; Song, X.; Milstein, D. J. Am. Chem. Soc. 2001, 123, 337-338
37. Ackermann, L.; Lygin, A. V.; Hofmann, N. Angew. Chem., Int. Ed. 2011, 50, 6379-6382
38. Ackermann, L.; Lygin, A. V.; Hofmann, N. Org. Lett. 2011, 13, 3278-3281
39. Ackermann, L.; Fenner, S. Org. Lett. 2011, 13, 6548-6551
40. Ackermann, L.; Pospech, J.; Graczyk, K.; Rauch, K. Org. Lett. 2012, 14, 930-933
41. Ackermann, L.; Wang, L.; Lygin, A. V. Chem. Sci. 2012, 3, 177-180
42. Chinnagolla, R. K.; Jeganmohan, M. Chem. Commun. 2012, 48, 2030-2032
43. Ackermann, L.; Lygin, A. V. Org. Lett. 2012, 14, 764-767
44. Parthasarathy, K.; Senthilkumar, N.; Jayakumar, J.; Cheng, C.-H. Org. Lett. 2012, 14, 3478-3481
45. Thirunavukkarasu, V. S.; Donati, M.; Ackermann, L. Org. Lett. 2012, 14, 3416-3419
46. An elegant rhodium-catalyzed olefination of arene esters was reported by Chang and coworkers: Park, S. H.; Kim, J. Y.; Chang, S. Org. Lett. 2011, 13, 2372-2375
47. Kakiuchi, F.; Ohtaki, H.; Sonoda, M.; Chatani, N.; Murai, S. Chem. Lett. 2001, 918-919
48. Neisius, N. M.; Plietker, B. Angew. Chem., Int. Ed. 2009, 48, 5752-5755 and references cited therein
49. Ackermann, L. Pure Appl. Chem. 2010, 82, 1403-1413
50. Ackermann, L. Isr. J. Chem. 2010, 50, 652-663
51. During the preparation of our manuscript a related independent study was disclosed: Padala, K.; Pimparkar, S.; Madasamy, P.; Jeganmohan, M. Chem. Commun. 2012, 48, 7140-7142
52. Ackermann, L.; Pospech, J.; Potukuchi, H. K. Org. Lett. 2012, 14, 2146-2149
53. Ackermann, L.; Diers, E.; Manvar, A. Org. Lett. 2012, 14, 1154-1157
54. Ackermann, L.; Lygin, A. Org. Lett. 2011, 13, 3332-3335
55. Ouellet, S. G.; Roy, A.; Molinaro, C.; Angelaud, R.; Marcoux, J.-F.; O'Shea, P. D.; Davies, I. W. J. Org. Chem. 2011, 76, 1436-1439
56. Ackermann, L.; Vicente, R.; Potukuchi, H. K.; Pirovano, V. Org. Lett. 2010, 12, 5032-5035
57. Ackermann, L.; Novák, P.; Vicente, R.; Hofmann, N. Angew. Chem., Int. Ed. 2009, 48, 6045-6048 and references cited therein
58. Ackermann, L. Chem. Rev. 2011, 111, 1315-1345