Catalytic intermolecular C-alkylation of 1,2-diketones with simple olefins: A recyclable directing group strategy

Journal of the American Chemical Society

Volumn 134, Issue 34, 2012, Pages 13954-13957

  Wang, Zhiqian ^a   Reinus, Brandon J ^a   Dong, Guangbin ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATING AGENTS; AMINOPYRIDINES; C-ALKYLATION; C-H BOND; ENAMINES; ONE POT; TERMINAL OLEFINS; UNACTIVATED OLEFINS; VINYL ESTERS;

ALKYLATION; FLAVOR COMPOUNDS; OLEFINS; ORGANIC COMPOUNDS; RHODIUM;

KETONES;

ACETYLACETONE; ALKENE DERIVATIVE; AMINOPYRIDINE; DIKETONE;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; HYDROLYSIS; ONE POT SYNTHESIS;

EID: 84865624028     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja306123m     Document Type: Article

References (36)

1. Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 1287
2. Jordan, R. F.; Taylor, D. F. J. Am. Chem. Soc. 1989, 111, 778
3. Moore, E. J.; Pretzer, W. R.; OConnell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimmer, S. S. J. Am. Chem. Soc. 1992, 114, 5888
4. Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature 1993, 366, 529
5. Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826
6. Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2012, 110, 624
7. Hartwig, J. F. Organotransition Metal Chemistry: From Bonding to Catalysis; University Science Books: 2010, pp 825-876.
8. Gonzalez-Rodriguez, C.; Willis, M. C. Pure Appl. Chem. 2011, 83, 577
9. Willis, M. C. Chem. Rev. 2010, 110, 725
10. Jun, C.-H.; Jo, E.-A.; Park, J.-W. Eur. J. Org. Chem. 2007, 12, 1869
11. Fu, G. C. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley: 2005, pp 79-91.
12. Jun, C.-H.; Lee, J. H. Pure Appl. Chem. 2004, 76, 577
13. Trost, B. M. Science 1991, 254, 1471
14. Pei, T.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11290
15. Widenhoefer, R. A. Pure Appl. Chem. 2004, 76, 671
16. For a radical-mediated ketone-olefin coupling, see: Iwahama, T.; Sakaguchi, S.; Ishii, Y. Chem. Commun. 2000, 2317
17. For a base-mediated enolate addition to styrenes, see: Rodriguez, A. L.; Bunlaksananusorn, T.; Knochel, P. Org. Lett. 2000, 2, 3285
18. For an addition of zinc enamides to unactivated olefins, see: Nakamura, M.; Hatakeyama, T.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 11820
19. Stuart, D. R.; Alsabeh, P.; Kuhn, M.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 18326
20. Hesp, K. D.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2011, 133, 11430
21. Rousseau, G.; Breit, B. Angew. Chem., Int. Ed. 2011, 50, 2450
22. Tan, K. L. Nat. Chem. 2012, 4, 253
23. Ponaras, A. A.; Meah, M. Y. Tetrahedron Lett. 2000, 9031 and references therein
24. Cuendet, M.; Pezzuto, J. M. J. Nat. Prod. 2004, 67, 269
25. Oka, M.; Iimura, S.; Tenmyo, O.; Sawada, Y.; Sugawara, M.; Ohkusa, H.; Yamamoto, H.; Kawano, K.; Hu, S. L.; Fukagawa, Y.; Oki, T. J. Antibiot. 1993, 46, 367
26. Strunz, G. M. J. Agric. Food Chem. 1983, 31, 185
27. Ponaras, A. A. J. Org. Chem. 1983, 48, 3866
28. Trost, B. M.; Schroeder, G. M. J. Am. Chem. Soc. 2000, 122, 3785
29. Kende, A. S.; Eilerman, R. G. Tetrahedron Lett. 1973, 697
30. Utaka, M.; Hojo, M.; Takeda, A. Chem. Lett. 1984, 445
31. For a CAN-mediated oxidative coupling of cyclic 1,2-diketones with electron-rich olefins, see: Miura, M.; Arai, N.; Narasaka, K. Bull. Chem. Soc. Jpn. 1998, 71, 1437
32. Suggs, J. W. J. Am. Chem. Soc. 1979, 101, 489
33. Zaitsev, V. G.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 4156
34. He, G.; Chen, G. Angew. Chem., Int. Ed. 2011, 50, 5192
35. Nishimura, O.; Mihara, S. J. Agric. Food Chem. 1990, 38, 1038
36. Arnarp, J.; Enzell, C.; Petersson, K.; Petersson, T. Acta Chem. Scand. B 1986, 40, 839