Ruthenium(II)-catalyzed regioselective synthesis of allyl ketones from alkynes and their silver (I)-catalyzed hydroarylation into γ- functionalized ketones

Advanced Synthesis and Catalysis

Volumn 351, Issue 10, 2009, Pages 1488-1494

  Zhang, Min ^a,b   Jiang, Huanfeng ^b   Dixneuf, Pierre H ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

^b SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

functionalized ketones; Allyl ketones; Atom economy; Ruthenium catalysts; Sequential catalysis; Silver catalysts

Indexed keywords

EID: 67650482833     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900236     Document Type: Article

References (58)

1. a) F. Kakiuchi, S. Murai, Acc. Chem. Res. 2002, 35, 826-834;
2. F. Kakiuchi, T. Kochi, Synthesis 2008, 3013-3039;
3. Handbook of C-H Transformations, (Ed.: G. Dyker), Wiley-VCH, Weinheim, 2005;
4. N. Chatani, Directed Metallation; in: Top. Organomet. Chem. Springer, Berlin, 2007, Vol 24, ppl-33;
5. V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731-1769;
6. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174-238.
7. For recent examples, see: a) T. Uemura, F. Kakiuchi, N. Chatani, Synlett., 2007, 170-172;
8. A. Martinez, R. Chevalier, S. Darses. J. P. Genet, Angew. Chem. 2006, 118, 8412-8415;
9. Angew. Chem. Int. Ed. 2006, 45, 8232-8235;
10. M. Q. Simon, R. Martinez, J. P. Genet, S. Darses, Adv. Synth. Catal. 2009, 351, 153-157;
11. R. Martinez, J. P. Genet, S. Darses, Chem. Commun. 2008, 3855-3857.
12. For reviews, see: a) T. B. Poulsen, K. A. Jørgensen, Chem. Rev. 2008, 108, 2903-2915;
13. M. Bandini, E. Emer, S. Tommasi, A. Umani-Ronchi, Eur. J. Org. Chem. 2006, 3527-3544;
14. M. Bandini, A. Melloni, V. Umani-Ronchi, Angew. Chem. 2004, 116, 560-566;
15. Angew. Chem. Int. Ed. 2004, 43, 550-556.
16. For recent papers, see: a) T. Arai, N. Yokoyama, Angew. Chem. 2008, 120, 5067-5070;
17. Angew. Chem. Int. Ed. 2008, 47, 4989-4992;
18. B. M. Trost, C. Muller, J. Am. Chem. Soc. 2008, 130, 2438-2439;
19. R. P. Herrera, V. Sgarzani, L. Bernardi, A. Ricci, Angew. Chem. 2005, 117, 6734-6737,
20. Angew. Chem. Int. Ed. 2005, 44, 6576-6579;
21. J.-R. Cheng, C.-F. Li, X.-L. An, J.-J. Zhang, X.-Y. Zhu, W.-J. Xiao, Angew. Chem. 2008, 120, 2523-2526;
22. Angew. Chem. Int. Ed. 2008, 47, 2489-2492;
23. P. K. Singh, V. K. Singh, Org. Lett, 2008, 4121-4124;
24. H. Huang, R. Peters, Angew. Chem. 2009, 121, 612-615;
25. Angew. Chem. Int. Ed. 2009, 48, 604-606;
26. M.-Z. Wang, M.-K. Wong, C.-M. Che, Chem. Eur. J. 2008, 14, 8353-8364;
27. S. W. Youn and J. I. Eom, J. Org. Chem. 2006, 71, 6705-6707;
28. P. Y. Toullec, E. Genin, L. Leseurre, J. P. Genêt, V. Michelet, Angew. Chem. 2006, 118, 7587-7590;
29. Angew. Chem. Int. Ed. 2006, 45, 7427-7430;
30. X. Zhao, Z. Yu, T. Xu, P. Wu, H. Yu, Org. Lett, 2007, 5263-5266;
31. J. Ichikawa, M. Yokota, T. Kudo, S. Umezaki, Angew. Chem. 2008, 120, 4948-4951;
32. Angew. Chem. Int. Ed. 2008, 47, 4870-4873;
33. M. A. Grundl, A. Kaster, E. D. Beaulieu, D. Trauner, Org. Lett, 2006, 5429-5432;
34. K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2008, 130, 14452-14453;
35. A. T. Luedtke, K. I. Goldberg, Angew. Chem. 2008, 120, 7808-7810;
36. Angew. Chem. Int. Ed. 2008, 47, 7694-7696.
37. I. Fernandez, R. Hermatschweiler, F. Breher, P. S. Pregosin, L. F. Veiros, M. J. Calhorda, Angew. Chem. 2006, 118, 6535-6540;
38. Angew. Chem. Int. Ed. 2006, 45, 6386-6391;
39. A. B. Zaitsev, S. Gruber, P. S. Pregosin, Chem. Commun. 2007, 4692-4693;
40. M. Kimura, M. Futamata, R. Mukai, Y. Tamaru, J. Am. Chem. Soc. 2005, 127, 4592-4593.
41. M. Bandini, A. Eichholzer, P. Kotrusz, M. Tragni, S. Troisi, A. Umani-Ronchi, Adv. Synth. Catal. 2009, 351, 319-324.
42. Allyl ketone preparations: a) via acylation: R. C. Larock, Y.-D. Lu, J. Org. Chem. 1993, 58, 2846-2850;
43. via addition to nitriles: A. S.-Y. Lee, L.-S. Lin, Tetrahedron Lett. 2000, 41, 8803-8806;
44. silyl enol addition: T. Ooi, R. Goto, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 10494-10495;
45. aubstitution of α-halo ketones: K. Takami, H. Yorimitsu, K. Oshima, Org. Lett. 2004, 6, 4555-4558;
46. J.-X. Wang, X. Jia, T. Meng, L. Xin, Synthesis 2005, 2838-2844;
47. S. Omura, T. Fukuyama, J. Horiguchi, Y. Murakami, I. Ryu, J. Am. Chem. Soc. 2008, 130, 14094-14095;
48. F. Shibahara, J. F. Bower, M. J. Krische, J. Am. Chem. Soc. 2008, 130, 14120-14122;
49. for a review, see: F. Shibahara, M. J. Krische, Chem. Lett. 2008, 37, 1102-1107.
50. For recent examples of Swern and Dess-Martin oxidation of homoallyl alcohols, see: a) P. R. Krishna, R. Srinivas, Tetrahedron: Asymmetry 2008, 19, 1153-1160;
51. B. M. Trost, H. Yang, O. R. Thiel, A. J. Frontier, C. S. Brindle, J. Am. Chem. Soc. 2007, 129, 2206-2207.
52. a) J. Le Paih, F. Monnier, S. Derien, P. H. Dixneuf, E. Clot, O. Eisenstein, J. Am. Chem. Soc. 2003, 125, 11964-11975.
53. M. Zhang, H. Jiang, H. Neumann, M. Beller, P. H. Dixneuf. Angew. Chem. Int. Ed. 2009, 45, 1681-1684.
54. M. O. Albers, D. J. A. de Waal, D. C. Liles, D. J. Robinson, E. Singleton, M. B. Wiege, J. Chem. Soc. Chem. Commun. 1986, 1680-1681.
55. B. M. Trost, M. Rudd, J. Am. Chem, Soc. 2003, 125, 11516-11517.
56. a) M. Naodovic, H. Yamamoto, Chem. Rev. 2008, 108, 3132-3314;
57. C. Alemparte, G. Blay, K. A. Jørgensen, Org. Lett. 2005, 7, 4569-4572;
58. A. Bottom, A. L. Costa, D. Di Tommaso, I. Rossi, E. Tagliavini, J. Am. Chem. Soc. 1997, 119, 12131-12135.