Rate enhanced olefin cross-metathesis reactions: The copper iodide effect

Journal of Organic Chemistry

Volumn 76, Issue 11, 2011, Pages 4697-4702

  Voigtritter, Karl ^a   Ghorai, Subir ^a   Lipshutz, Bruce H ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINATED SOLVENT; COCATALYST; COPPER IODIDE; CROSS-COUPLED; DIETHYL ETHERS; IODIDE ION; MICHAEL ACCEPTORS; OLEFIN CROSS-METATHESIS; REFLUXING; ROOM TEMPERATURE; STABILIZING EFFECTS;

CATALYSTS; ETHERS; OLEFINS; PHOSPHORUS COMPOUNDS; SURFACE ACTIVE AGENTS;

COPPER;

ALKENE; COPPER; ETHER; IODIDE; SOLVENT; SURFACTANT; WATER;

ARTICLE; CATALYST; CHLORINATION; CROSS COUPLING REACTION; ROOM TEMPERATURE;

ALKENES; CATALYSIS; COPPER; IODIDES; KINETICS;

EID: 79957850855     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200360s     Document Type: Article

References (50)

1. Chauvin, Y. Angew. Chem., Int. Ed. 2006, 45, 3740-3747
2. Schrock, R. R. Angew. Chem., Int. Ed. 2006, 45, 3748-3759
3. Grubbs, R. H. Angew. Chem., Int. Ed. 2006, 45, 3760-3765
4. Grubbs, R. H. Tetrahedron 2004, 60, 7117-7140
5. Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003, (three-volume set).
6. For a review, see: Schrodi, Y.; Pederson, R. L. Aldrichim. Acta 2007, 40, 45-52
7. Fürstner, A.; Thiel, O. R.; Lehmann, C. W. Organometallics 2002, 21, 331-335
8. Jafarpour, L.; Hillier, A. C.; Nolan, S. P. Organometallics 2002, 21, 442-444
9. Wakamatsu, H.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 2403-2405
10. Grela, K.; Harutyunyan, S.; Michrowska, A. Angew. Chem., Int. Ed. 2002, 41, 4038-4040
11. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956
12. Morgan, J. P.; Morrill, C.; Grubbs, R. H. Org. Lett. 2002, 4, 67-70
13. Chatterjee, A. K.; Sanders, D. P.; Grubbs, R. H. Org. Lett. 2002, 4, 1939-1942
14. Lera, M.; Hayes, C. J. Org. Lett. 2001, 3, 2765-2768
15. Stragies, R.; Voigtmann, U.; Blechert, S. Tetrahedron Lett. 2000, 41, 5465-5468
16. Ettari, R.; Micale, N. J. Organomet. Chem. 2007, 692, 3574-3576
17. Michrowska, A.; Bujok, R.; Harutyunyan, S.; Sashuk, V.; Dolgonos, G.; Grela, K. J. Am. Chem. Soc. 2004, 126, 9318-9325
18. Choi, T.-L.; Chatterjee, A. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2001, 40, 1277-1279
19. Lipshutz, B. H.; Ghorai, S.; Bošković, Z. V. Tetrahedron 2008, 64, 6949-6954
20. Lipshutz, B. H.; Aguinaldo, G. T.; Ghorai, S.; Voigtritter, K. Org. Lett. 2008, 10, 1325-1328
21. Lipshutz, B. H.; Ghorai, S.; Leong, W. W. Y. J. Org. Chem. 2009, 74, 2854-2857
22. Boddaert, T.; Coquerel, Y.; Rodriguez, J. C. R. Chim. 2009, 12, 872-875
23. Rivard, M.; Blechert, S. Eur. J. Org. Chem. 2003, 2225-2228
24. Lipshutz, B. H.; Ghorai, S. Org. Lett. 2009, 11, 705-708
25. Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J., Jr.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791-799
26. Lipshutz, B. H.; Ghorai, S. Tetrahedron 2010, 66, 1057-1063
27. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179
28. Morgan, J. P.; Grubbs, R. H. Org. Lett. 2000, 2, 3153-3155
29. Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887-3897
30. Sanford, M. S.; Henling, L. M.; Grubbs, R. H. Organometallics 1998, 17, 5384-5389
31. Funk, T. W.; Berlin, J. M.; Grubbs, R. H. J. Am. Chem. Soc. 2006, 128, 1840-1846
32. Wappel, J.; Urbina-Blanco, C. A.; Abbas, M.; Albering, J. H.; Saf, R.; Nolan, S. P.; Slugovc, C. Beilstein J. Org. Chem. 2010, 6, 1091-1098
33. Stewart, I. C.; Ung, T.; Pletnev, A. A.; Berlin, J. M.; Grubbs, R. H.; Schrodi, Y. Org. Lett. 2007, 9, 1589-1592
34. Hurley, P. B.; Dake, G. R. J. Org. Chem. 2008, 73, 4131-4138
35. Verpoort, F.; Opstal, T. New J. Chem. 2003, 27, 257-262
36. Numerous previous attempts (by varying reaction temperature and the amount of catalyst) to drive this coupling beyond the 55% reported had not been successful. See ref 8a.
37. Poulsen, C. S.; Madsen, R. Synthesis 2003, 1-18
38. Mori, M. Ene-Yne Metathesis. In Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003; Vol. 2, pp 176-204.
39. Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317-1382
40. Clark, D. A.; Clark, J. R.; Diver, S. T. Org. Lett. 2008, 10, 2055-2058
41. Donohoe, T. J.; Bower, J. F. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 3373-3376
42. Bai, C.-X.; Lu, X.-B.; He, R.; Zhang, W.-Z.; Feng, X.-J. Org. Biomol. Chem. 2005, 3, 4139-4142
43. Coquerel, Y.; Rodriguez, J. Eur. J. Org. Chem. 2008, 1125-1132
44. Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-11370
45. Okamoto, T.; Kawasaki, T.; Hino, O. Biochem. Pharmacol. 2003, 65, 677-681
46. TPGS-750-M will be offered in February, 2011, as a 2 wt % solution in water by Sigma-Aldrich. This product will be listed under catalog no. 733857.
47. Lipshutz, B. H.; Ghorai, S.; Abela, A. R.; Moser, R.; Nishikata, T.; Duplais, C.; Krasovskiy, A.; Gatson, R. D.; Gadwood, R. C. J. Org. Chem. 2011, DOI: (http://dx.doi.org/10.1021/jo101974u)
48. Dwars, T.; Paetzold, E.; Oehme, G. Angew. Chem., Int. Ed. 2005, 44, 7174-7199
49. Khan, M. N. Micellar Catalysis; CRC Press: Boca Raton, FL, 2006.
50. Sheldon, R. A.; Arends, I. W. C. E.; Hanefeld, U. Green Chemistry and Catalysis; Wiley-VCH: Weinheim, Germany, 2007.