Molybdenum-based complexes with two aryloxides and a pentafluoroimido ligand: Catalysts for efficient z-selective synthesis of a macrocyclic trisubstituted alkene by ring-closing metathesis

Angewandte Chemie - International Edition

Volumn 52, Issue 7, 2013, Pages 1939-1943

  Wang, Chenbo ^a   Haeffner, Fredrik ^a   Schrock, Richard R ^b   Hoveyda, Amir H ^a  

^a BOSTON COLLEGE   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

homogeneous catalysis; macrocycles; olefin metathesis; ring closing metathesis; trisubstituted olefins

Indexed keywords

ALKYLIDENES; ANTI-CANCER AGENTS; ARYLOXIDE LIGANDS; EPOTHILONES; HOMOGENEOUS CATALYSIS; MACROCYCLES; MACROCYCLIC LACTONES; MACROCYCLICS; OLEFIN METATHESIS; RING CLOSING METATHESIS; ROOM TEMPERATURE; TRISUBSTITUTED ALKENES; Z SELECTIVITIES;

CATALYSTS; LIGANDS; MOLYBDENUM COMPOUNDS; REACTION KINETICS;

OLEFINS;

ALKENE; COORDINATION COMPOUND; DESOXYEPOTHILONE B; EPOTHILONE B; EPOTHILONE DERIVATIVE; IMINE; LIGAND; MACROCYCLIC COMPOUND; MOLYBDENUM; OXIDE;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS; TEMPERATURE;

ALKENES; CATALYSIS; COORDINATION COMPLEXES; EPOTHILONES; IMINES; LIGANDS; MACROCYCLIC COMPOUNDS; MOLYBDENUM; OXIDES; TEMPERATURE;

EID: 84873545747     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201209180     Document Type: Article

References (43)

1. A. H. Hoveyda, A. R. Zhugralin, Nature 2007, 450, 243.
2. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. 2005, 117, 4564
3. Angew. Chem. Int. Ed. 2005, 44, 4490
4. A. Gradillas, J. Pérez-Castells, Angew. Chem. 2006, 118, 6232
5. Angew. Chem. Int. Ed. 2006, 45, 6086.
6. M. Yu, C. Wang, A. F. Kyle, P. Jakubec, D. J. Dixon, R. R. Schrock, A. H. Hoveyda, Nature 2011, 479, 88
7. C. Wang, M. Yu, A. F. Kyle, P. Jakubec, D. J. Dixon, R. R. Schrock, A. H. Hoveyda, Chem. Eur. J. DOI:.
8. A. Fürstner, P. W. Davis, Chem. Commun. 2005, 2307
9. W. Zhang, J. S. Moore, Adv. Synth. Catal. 2007, 349, 93.
10. K. C. Nicolaou, H. Xu, Chem. Commun. 2006, 600
11. P. K. Park, S. J. O'Malley, D. R. Schmidt, J. L. Leighton, J. Am. Chem. Soc. 2006, 128, 2796
12. R. Tannert, T.-S. Hu, H.-S. Arndt, H. Waldmann, Chem. Commun. 2009, 1493.
13. A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, J. Am. Chem. Soc. 1995, 117, 2943
14. H. Fuwa, A. Saito, M. Sasaki, Angew. Chem. 2010, 122, 3105
15. Angew. Chem. Int. Ed. 2010, 49, 3041.
16. A. B. Smith III, E. F. Mesaros, E. A. Meyer, J. Am. Chem. Soc. 2006, 128, 5292
17. T. Gaich, H. Weinstabl, J. Mulzer, Synlett 2009, 1357.
18. T. R. Hoye, H. Zhao, Org. Lett. 1999, 1, 169
19. B. Schmidt, Eur. J. Org. Chem. 2004, 1865
20. M. Michalak, J. Wicha, Org. Biomol. Chem. 2011, 9, 3439
21. Z. Cai, N. Yongpruksa, M. Harmata, Org. Lett. 2012, 14, 1661.
22. For an early examination of the reversibility of macrocyclic RCM reactions, see:, Z. Xu, C. W. Johannes, A. F. Houri, D. S. La, D. A. Cogan, G. E. Hofilena, A. H. Hoveyda, J. Am. Chem. Soc. 1997, 119, 10302.
23. G. Höfle, N. Bedorf, H. Steinmetz, D. Schomburg, K. Gerth, H. Reichenbach, Angew. Chem. 1996, 108, 1671
24. Angew. Chem. Int. Ed. Engl. 1996, 35, 1567
25. K. C. Nicolaou, F. Roschangar, D. Vourloumis, Angew. Chem. 1998, 110, 2120
26. Angew. Chem. Int. Ed. 1998, 37, 2014
27. A. Rivkin, T.-C. Chou, S. J. Danishefsky, Angew. Chem. 2005, 117, 2898
28. Angew. Chem. Int. Ed. 2005, 44, 2838
29. K. H. Altmann, B. Pfeiffer, S. Arseniyadis, B. A. Pratt, K. C. Nicolaou, ChemMedChem 2007, 2, 396.
30. R. Singh, R. R. Schrock, P. Müller, A. H. Hoveyda, J. Am. Chem. Soc. 2007, 129, 12654
31. S. J. Malcolmson, S. J. Meek, E. S. Sattely, R. R. Schrock, A. H. Hoveyda, Nature 2008, 456, 933
32. I. Ibrahem, M. Yu, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 3844.
33. S. J. Meek, R. V. O'Brien, J. Llaveria, R. R. Schrock, A. H. Hoveyda, Nature 2011, 471, 461.
34. For Z-selective macrocyclic RCM reactions involving silyl-substituted trisubstituted alkenes, see:, Y. Wang, M. Jiminez, A. S. Hansen, E.-A. Raiber, S. L. Schreiber, D. W. Young, J. Am. Chem. Soc. 2011, 133, 9196.
35. K. C. Nicolaou, Y. He, D. Vourloumis, H. Vallberg, F. Roschangar, F. Sarabia, S. Ninkovic, Z. Yang, J. I. Trujillo, J. Am. Chem. Soc. 1997, 119, 7960
36. D. Schinzer, A. Bauer, J. Scheiber, Chem. Eur. J. 1999, 5, 2492.
37. D. Meng, P. Bertinato, A. Balog, D.-S. Su, T. Kamenecka, E. J. Sorensen, S. J. Danishefsky, J. Am. Chem. Soc. 1997, 119, 10073
38. S. C. Sinha, J. Sun, G. P. Miller, M. Wartmann, R. A. Lerner, Chem. Eur. J. 2001, 7, 1691.
39. M. Yu, I. Ibrahem, M. Hasegawa, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc. 2012, 134, 2788.
40. E. S. Sattely, S. J. Meek, S. J. Malcolmson, R. R. Schrock, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 943.
41. J. Yuan, R. R. Schrock, P. Müller, J. C. Axtell, G. E. Dobereiner, Organometallics 2012, 31, 4650.
42. -1); see:, A. Poater, X. Solans-Monfort, E. Clot, C. Copéret, O. Eisenstein, J. Am. Chem. Soc. 2007, 129, 8207. The higher stability of the unsubstituted metallacyclobutanes accounts for the increased efficiency when ethylene is removed under vacuum (cf. entries 5-6, Table 2).
43. Such relative stability is likely due to an increase in the energy of the square-based pyramidal complexes, supposedly involved in catalyst decomposition pathways, by the electron-donating pyrrolide ligand. See:, X. Solans-Monfort, C. Copéret, O. Eisenstein, J. Am. Chem. Soc. 2010, 132, 7750.