Glycerol - A non-innocent solvent for Rh-catalysed Pauson-Khand carbocyclisations

European Journal of Inorganic Chemistry

Volumn , Issue 29, 2013, Pages 5138-5144

  Chahdoura, Faouzi ^a   Dubrulle, Laurent ^a,b   Fourmy, Kevin ^b   Durand, Jérôme ^b   Madec, David ^a   Gõmez, Montserrat ^a  

^a UNIVERSITÉ PAUL SABATIER   (France)

^b LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

C C coupling; Glycerol; NMR spectroscopy; Reaction mechanisms; Rhodium

Indexed keywords

CATALYSIS; GLYCEROL; LIGANDS; RHODIUM COMPOUNDS;

C-C COUPLING; CARBOCYCLIZATION; CATALYST PERFORMANCE; CATALYTIC PROCESS; LIGAND-FREE; NMR STUDIES; NMR-SPECTROSCOPY; PAUSON-KHAND; PHOSPHANES; REACTION MECHANISM;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 84885107126     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.201300651     Document Type: Article

References (47)

1. R. A. Sheldon, J. Mol. Catal. A 1996, 107, 75-83.
2. R. A. Sheldon, Pure Appl. Chem. 2000, 72, 1233-1246.
3. P. T. Anastas, J. B. Zimmerman, Environ. Sci. Technol. 2003, 37, 94A-101A.
4. P. T. Anastas, M. M. Kirchhoff, Acc. Chem. Res. 2002, 35, 686-694.
5. P. Anastas, J. Warner, in: Green Chemistry: Theory and Practice, Oxford University Press, New York, 1998.
6. W. Leitner, Acc. Chem. Res. 2002, 35, 746-756.
7. S. Liu, J. Xiao, J. Mol. Catal. A 2007, 270, 1-43.
8. M. Gõmez, E. Teuma, J. Durand, C. R. Chim. 2007, 10, 152-177.
9. R. K. Henderson, C. Jiménez-González, D. J. C. Constable, S. R. Alston, G. G. A. Inglis, G. Fisher, J. Sherwood, S. P. Binks, A. D. Curzons, Green Chem. 2011, 13, 854-862.
10. M. J. Raymond, C. S. Slater, M. J. Savelski, Green Chem. 2010, 12, 1826-1834.
11. I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, J. Chem. Soc., Chem. Commun. 1971, 36-36. For preliminary mechanistical discussion, see
12. P. Magnus, L. M. Principe, Tetrahedron Lett. 1985, 26, 4851-4854. For a first example of intramolecular reaction, see
13. N. E. Schore, M. C. Croudace, J. Org. Chem. 1981, 46, 5436-5438. For reviews, see
14. P. L. Pauson, Tetrahedron 1985, 41, 5855-5860.
15. N. E. Schore, Org. React. 1991, 40, 1-90.
16. S. E. Gibson, N. Mainolfi, Angew. Chem. 2005, 117, 3082;
17. Angew. Chem. Int. Ed. 2005, 44, 3022-3037.
18. H.-W. Lee, F.-Y. Kwong, Eur. J. Org. Chem. 2010, 789-811.
19. The Pauson-Khand Reaction. Scope, Variations and Applications (Ed.:, R. R. Torres), Wiley-VCH, Weinheim, Germany, 2012.
20. A. Corma, S. Iborra, A. Velty, Chem. Rev. 2007, 107, 2411-2502.
21. Y. Zheng, X. Chen, Y. Shen, Chem. Rev. 2008, 108, 5253-5277.
22. Y. Gu, F. Jérôme, Green Chem. 2010, 12, 1127-1138.
23. A. E. Diaz-Alvarez, J. Francos, B. Lastra-Barreira, P. Crochet, V. Cadierno, Chem. Commun. 2011, 47, 6208-6227.
24. T. Kobayashi, Y. Koga, K. Narasaka, J. Organomet. Chem. 2001, 624, 73-87.
25. E. Kim, I. S. Kim, V. Ratovelomanana-Vidal, J.-P. Genêt, N. Jeong, J. Org. Chem. 2008, 73, 7985-7989.
26. J. H. Park, Y. Cho, Y. K. Chung, Angew. Chem. 2010, 122, 5264;
27. Angew. Chem. Int. Ed. 2010, 49, 5138-5141.
28. K. Ikeda, T. Morimoto, K. Kakiuchi, J. Org. Chem. 2010, 75, 6279-6282.
29. T. Morimoto, K. Fuji, K. Tsutsumi, K. Kakiuchi, J. Am. Chem. Soc. 2002, 124, 3806-3807.
30. K. Fuji, T. Morimoto, K. Tsutsumi, K. Kakiuchi, Angew. Chem. 2003, 115, 2511;
31. Angew. Chem. Int. Ed. 2003, 42, 2409-2411.
32. T. Shibata, N. Toshida, K. Tagagi, Org. Lett. 2002, 4, 1619-1621.
33. T. Shibata, N. Toshida, K. Tagagi, J. Org. Chem. 2002, 67, 7446-7450.
34. F. Y. Kwong, Y. M. Li, W. H. Lam, L. Qiu, H. W. Lee, C. H. Yeung, K. S. Chan, A. S. C. Chan, Chem. Eur. J. 2005, 11, 3872-3880.
35. F. Y. Kwong, H. W. Lee, L. Qiu, W. H. Lam, Y. M. Li, H. L. Kwong, A. S. C. Chan, Adv. Synth. Catal. 2005, 347, 1750-1754.
36. D. E. Kim, V. Ratovelomanana-Vidal, N. Jeong, Adv. Synth. Catal. 2010, 352, 2032-2040.
37. a(glycerol) = 14.4., W. L. F. Armarego, C. L. Lin Chai, in: Purification of Laboratory Chemicals, 6th ed., Elsevier, Oxford, 2009.
38. K. Angermund, W. Baumann, E. Dinjus, R. Fornika, H. Görls, M. Kessler, C. Krüger, W. Leitner, F. Lutz, Chem. Eur. J. 1997, 3, 755-764.
39. G. Lamb, M. Clarke, A. M. Z. Slawin, B. Williams, L. Key, Dalton Trans. 2007, 5582-5589.
40. D. A. Slack, I. Greveling, M. C. Baird, Inorg. Chem. 1979, 18, 3125-3132.
41. For the mechanistic role of thf in the PKR, see:, Y. H. Choi, J. Kwak, N. Jeong, Tetrahedron Lett. 2009, 50, 6068-6071.
42. T. Kobayashi, Y. Koga, K. Narasaka, J. Organomet. Chem. 2001, 624, 73-87.
43. A. J. Pearson, R. A. Dubbert, J. Chem. Soc., Chem. Commun. 1991, 202-203.
44. H. W. Lee, L. N. Lee, A. S. C. Chan, F. Y. Kwong, Eur. J. Org. Chem. 2008, 3403-3406.
45. Y. Tang, L. Deng, Y. Zhnag, G. Dong, J. Chen, Z. Yang, Org. Lett. 2005, 7, 1657-1659.
46. R. Usõn, L. A. Oro, J. A. Cabeza, Inorg. Synth. 1985, 23, 126-130.
47. F. Y. Kwong, H. W. Lee, L. Qiu, W. H. Lam, Y.-M. Li, H. L. Kwong, A. S. C. Chan, Adv. Synth. Catal. 2005, 347, 1750-1754.