Successive C-C coupling of dienes to vicinally dioxygenated hydrocarbons: Ruthenium catalyzed [4 + 2] cycloaddition across the diol, hydroxycarbonyl, or dione oxidation levels

Journal of the American Chemical Society

Volumn 135, Issue 10, 2013, Pages 3796-3799

  Geary, Laina M ^a   Glasspoole, Ben W ^a   Kim, Mary M ^a   Krische, Michael J ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

[4 + 2] CYCLOADDITION; C-C COUPLING; CARBONYL ADDITION; OXIDATION LEVEL; OXIDATIVE COUPLINGS; RUTHENIUMS (0);

KETONES; RUTHENIUM;

OLEFINS;

ALCOHOL DERIVATIVE; ALKADIENE; CARBONYL DERIVATIVE; HYDROCARBON; KETONE DERIVATIVE; RUTHENIUM COMPLEX;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; CYCLOADDITION; GEL CHROMATOGRAPHY; MOLECULAR MODEL; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY DIFFRACTION;

ALCOHOLS; ALDEHYDES; ALKADIENES; CATALYSIS; CYCLIZATION; HYDROCARBONS, AROMATIC; KETONES; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; RUTHENIUM;

EID: 84874973959     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja400691t     Document Type: Article

References (40)

1. Ragauskas, A. J.; Williams, C. K.; Davison, B. H.; Britovsek, G.; Cairney, J.; Eckert, C. A.; Frederick, W. J., Jr.; Hallett, J. P.; Leak, D. J.; Liotta, C. L.; Mielenz, J. R.; Murphy, R.; Templer, R.; Tschaplinski, T. Science 2006, 311, 484
2. Sheldon, R. A. Catal. Today 2011, 167, 3
3. Gallezot, P. Chem. Soc. Rev. 2012, 41, 1538
4. Dapsens, P. Y.; Mondelli, C.; Perez-Ramirez, J. ACS Catal. 2012, 2, 1487
5. Gable, K. P.; Juliette, J. J. J. Am. Chem. Soc. 1996, 118, 2625
6. Cook, G. K.; Andrews, M. A. J. Am. Chem. Soc. 1996, 118, 9448
7. Ziegler, J. E.; Zdilla, M. J.; Evans, A. J.; Abu-Omar, M. M. Inorg. Chem. 2009, 48, 9998
8. Vkuturi, S.; Chapman, G.; Ahmad, I.; Nicholas, K. M. Inorg. Chem. 2010, 49, 4744
9. Ahmad, I.; Chapman, G.; Nicholas, K. M. Organometallics 2011, 30, 2810
10. Bower, J. F.; Krische, M. J. Top. Organomet. Chem. 2011, 43, 107
11. Hassan, A.; Krische, M. J. Org. Process Res. Dev. 2011, 15, 1236
12. Moran, J.; Krische, M. J. Pure Appl. Chem. 2012, 84, 1729
13. Leung, J. C.; Geary, L. M.; Chen, T.-Y.; Zbieg, J. R.; Krische, M. J. J. Am. Chem. Soc. 2012, 134, 15700
14. Nakao, Y.; Morita, E.; Idei, H.; Hiyama, T. J. Am. Chem. Soc. 2011, 133, 3264
15. Stang, E. M.; White, M. C. J. Am. Chem. Soc. 2011, 133, 14892
16. Masato, O.; Ippei, T.; Masashi, I.; Sensuke, O. J. Am. Chem. Soc. 2011, 133, 18018
17. Herath, A.; Montgomery, J. J. Am. Chem. Soc. 2006, 128, 14030
18. Chang, H.-T.; Jayanth, T. T.; Cheng, C.-H. J. Am. Chem. Soc. 2007, 129, 4166
19. Williams, V. M.; Kong, J.-R.; Ko, B.-J.; Mantri, Y.; Brodbelt, J. S.; Baik, M.-H.; Krische, M. J. J. Am. Chem. Soc. 2009, 131, 16054
20. Jenkins, A. D.; Herath, A.; Song, M.; Montgomery, J. J. Am. Chem. Soc. 2011, 133, 14460
21. Ohashi, M.; Taniguchi, T.; Ogoshi, S. J. Am. Chem. Soc. 2011, 133, 14900
22. Wei, C.-H.; Mannathan, S.; Cheng, C.-H. Angew. Chem., Int. Ed. 2012, 51, 10592
23. Kaspar, J.; Spogliarich, R.; Graziani, M. J. Organomet. Chem. 1985, 281, 299
24. Hilal, H. S.; Khalaf, S.; Jondi, W. J. Organomet. Chem. 1993, 452, 167
25. Jun, C.-H.; Lee, H.; Park, J.-B.; Lee, D.-Y. Org. Lett. 1999, 1, 2161
26. Alvila, L.; Pakkanen, T. A.; Krause, O. J. Mol. Catal. 1993, 84, 145
27. 3(dppe): Sanchez-Delgado, R. A.; Bradley, J. S.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1976, 399
28. Blum, Y.; Reshef, D.; Shvo, Y. Tetrahedron Lett. 1981, 22, 1541
29. Shvo, Y.; Blum, Y.; Reshef, D.; Menzin, M. J. Organomet. Chem. 1982, 226, C21
30. Meijer, R. H.; Ligthart, G. B. W. L.; Meuldijkb, J.; Vekemans, J. A. J. M.; Hulshof, L. A.; Mills, A. M.; Kooijmanc, H.; Spek, A. L. Tetrahedron 2004, 60, 1065
31. 12 catalyzed transfer hydrogenation of ketones mediated by isopropanol, see: Johnson, T. C.; Totty, W. G.; Wills, M. Org. Lett. 2012, 14, 5230
32. Baehn, S.; Tillack, A.; Imm, S.; Mevius, K.; Michalik, D.; Hollmann, D.; Neubert, L.; Beller, M. ChemSusChem 2009, 2, 551
33. Pingen, D.; Müller, C.; Vogt, D. Angew. Chem., Int. Ed. 2010, 49, 8130
34. Zhang, M.; Imm, S.; Bahn, S.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2011, 50, 11197
35. Chatani, N.; Tobisu, M.; Asaumi, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1999, 121, 7160
36. Tobisu, M.; Chatani, N.; Asaumi, T.; Amako, K.; Ie, Y.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 2000, 122, 12663
37. Ciamician, G.; Silber, P. Chem. Ber. 1908, 41, 1928
38. Diels, O.; Alder, K. Ann 1928, 460, 98
39. For a review of metal catalyzed cycloadditions, see: Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49
40. For a review of "redox economy", see: Baran, P. S.; Hoffmann, R. W.; Burns, N. Z. Angew. Chem., Int. Ed. 2009, 48, 2854