C-C bond formation with carbon dioxide promoted by a silver catalyst

Angewandte Chemie - International Edition

Volumn 51, Issue 28, 2012, Pages 6989-6992

  Kikuchi, Satoshi ^a   Sekine, Kohei ^a   Ishida, Tomonobu ^a   Yamada, Tohru ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

C C bond formation; carbon dioxide; homogeneous catalysis; silver; synthetic methods

Indexed keywords

ALKYNE GROUPS; C-C BOND FORMATION; CATALYTIC AMOUNTS; CATALYTIC SYSTEM; HIGH YIELD; HOMOGENEOUS CATALYSIS; SILVER CATALYST; SYNTHETIC METHODS;

ACETYLENE; KETONES; REACTION KINETICS; SILVER;

CARBON DIOXIDE;

EID: 84863683008     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201201399     Document Type: Article

References (37)

1. T. Sakakura, J. C. Choi, H. Yasuda, Chem. Rev. 2007, 107, 2365-2387
2. T. Sakakura, K. Kohno, Chem. Commun. 2009, 1312-1330.
3. I. Mutule, E. Suna, Tetrahedron 2005, 61, 11168-11176
4. D. Y. Tang, A. Lipman, G. J. Meyer, C. N. Wan, A. P. Wolf, J. Labelled Compd. Radiopharm. 1979, 16, 435-440.
5. W. Neugebauer, T. Clark, P. v. R. Schleyer, Chem. Ber. 1983, 116, 3283-3292
6. E. J. Soloski, C. Tamborski, J. Organomet. Chem. 1978, 157, 373-377.
7. P. Braunstein, D. Matt, D. Nobel, Chem. Rev. 1988, 88, 747-764
8. J. Louie, Curr. Org. Chem. 2005, 9, 605-623
9. A. Correa, R. Martín, Angew. Chem. 2009, 121, 6317-6320
10. Angew. Chem. Int. Ed. 2009, 48, 6201-6204
11. S. N. Riduan, Y. Zhang, Dalton Trans. 2010, 39, 3347-3357
12. I. I. F. Boogaerts, S. P. Nolan, Chem. Commun. 2011, 47, 3021-3024
13. Y. Zhang, S. N. Riduan, Angew. Chem. 2011, 123, 6334-6336
14. Angew. Chem. Int. Ed. 2011, 50, 6210-6212
15. S. Li, W. Yuan, S. Ma, Angew. Chem. 2011, 123, 2626-2630
16. Angew. Chem. Int. Ed. 2011, 50, 2578-2582
17. M. Cokoja, C. Bruckmeier, B. Rieger, W. A. Herrmann, F. E. Fühn, Angew. Chem. 2011, 123, 8662-8690
18. Angew. Chem. Int. Ed. 2011, 50, 8510-8537.
19. J. Louie, J. E. Gibby, M. V. Farnworth, T. N. Tekavec, J. Am. Chem. Soc. 2002, 124, 15188-15189
20. W. Z. Zhang, W. J. Li, X. Zhang, H. Zhou, X. B. Lu, Org. Lett. 2010, 12, 4748-4751
21. L. Zhang, J. Cheng, T. Ohishi, Z. Hou, Angew. Chem. 2010, 122, 8852-8855
22. Angew. Chem. Int. Ed. 2010, 49, 8670-8673
23. I. I. F. Boogaerts, S. P. Nolan, J. Am. Chem. Soc. 2010, 132, 8858-8859
24. O. Vechorkin, N. Hirt, X. Hu, Org. Lett. 2010, 12, 3567-3569
25. I. I. F. Boogaerts, G. C. Fortman, M. R. L. Furst, C. S. J. Cazin, S. P. Nolan, Angew. Chem. 2010, 122, 8856-8859
26. Angew. Chem. Int. Ed. 2010, 49, 8674-8677
27. X. Zhang, W. Z. Zhang, X. Ren, L. L. Zhang, X. B. Lu, Org. Lett. 2011, 13, 2402-2405
28. K. Inamoto, N. Asano, K. Kobayashi, M. Yonemoto, Y. Kondo, Org. Biomol. Chem. 2012, 10, 1514-1516.
29. E. J. Corey, R. H. K. Chen, J. Org. Chem. 1973, 38, 4086
30. K. Chiba, H. Tagaya, S. Miura, M. Karasu, Chem. Lett. 1992, 923
31. E. Haruki, M. Arakawa, N. Matsumura, Y. Otsuji, E. Imoto, Chem. Lett. 1974, 427-428
32. B. J. Flowers, R. Gautreau-Service, P. G. Jessop, Adv. Synth. Catal. 2008, 350, 2947-2958.
33. W. Yamada, Y. Sugawara, H. M. Cheng, T. Ikeno, T. Yamada, Eur. J. Org. Chem. 2007, 2604-2607.
34. Y. Sugawara, W. Yamada, S. Yoshida, T. Ikeno, T. Yamada, J. Am. Chem. Soc. 2007, 129, 12902-12903.
35. S. Kikuchi, S. Yoshida, Y. Sugawara, W. Yamada, H. M. Cheng, K. Fukui, K. Sekine, I. Iwakura, T. Ikeno, T. Yamada, Bull. Chem. Soc. Jpn. 2011, 84, 698-717.
36. S. Yoshida, K. Fukui, S. Kikuchi, T. Yamada, J. Am. Chem. Soc. 2010, 132, 4072-4073.
37. It was reported that the dihydrofuran derivatives were formed in the presence of an acid catalyst at high temperature. See:, Z. P. Zhan, S. P. Wang, X. B. Cai, H. J. Liu, J. L. Yu, Y. Y. Cuia, Adv. Synth. Catal. 2007, 349, 2097-2102.