Characterization and dynamics of substituted ruthenacyclobutanes relevant to the olefin cross-metathesis reaction

Journal of the American Chemical Society

Volumn 133, Issue 16, 2011, Pages 6429-6439

  Wenzel, Anna G ^a   Blake, Garrett ^a   Vandervelde, David G ^b   Grubbs, Robert H ^b  

^a SCRIPPS COLLEGE   (United States)

^b California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1-BUTENE; 1-HEXENE; ALKYLIDENES; BENZYLIDENE; CHEMICAL EXCHANGE; DIRECT PREPARATION; ETHYLENE CONCENTRATION; EXCHANGE PROCESS; METALLACYCLES; METHYLENE GROUPS; OLEFIN CROSS-METATHESIS; OLEFIN METATHESIS; PROTON SOURCE; PROTONOLYSIS; REACTION TIME; TIME-SCALES; TRIFLUOROACETIC ACIDS;

ACTIVATION ENERGY; BUTENES; CHLORINE; ETHYLENE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROPYLENE; RUTHENIUM; RUTHENIUM COMPOUNDS; SILICA; STEREOCHEMISTRY;

CHEMICAL REACTIONS;

3 BROMOPYRIDINE DERIVATE; ALKENE; CARBENE; CYCLOBUTANE DERIVATIVE; DICHLORO[1,3 BIS(2,4,6 TRIMETHYLPHENYL) 2 IMIDAZOLIDINYLIDEN) (BENZYLIDEN)]BIS(PYRIDIN)RUTHENIUM II; ETHYLENE; HYDROGEN; PROTON; PYRIDINE DERIVATIVE; RUTHENACYCLOBUTANE; RUTHENIUM DERIVATIVE; SILICON DIOXIDE; TOLUENESULFONIC ACID DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CONCENTRATION (PARAMETERS); CROSS METATHESIS REACTION; ENERGY; MOLECULAR DYNAMICS; STEREOCHEMISTRY; STEREOISOMERISM;

CYCLIZATION; CYCLOBUTANES; MAGNETIC RESONANCE SPECTROSCOPY; RUTHENIUM COMPOUNDS;

EID: 79954994095     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2009746     Document Type: Article

References (72)

1. Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003; Vols. 1-3.
2. Ivin, K. J. and Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: San Diego, CA, 1997.
3. Green Metathesis Chemistry: Great Challenges in Synthesis, Catalysis and Nanotechnology (NATO Science for Peace and Security Series A: Chemistry and Biology); Dragutan, V., Demonceau, A., Dragutan, I., and Finkelshtein, E. S., Eds.; Springer: Dordrecht, The Netherlands, 2009.
4. Metathesis Polymerization of Olefins and Polymerization of Alkynes (NATO Science Series C); Imamogammalu, Y., Ed.; Springer: Dordrecht, the Netherlands, 2009.
5. Grubbs, R. H. Tetrahedron 2004, 60, 7117-7140
6. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29
7. Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543-6554
8. Sanford, M. S.; Ulman, M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 749-750
9. Kingsbury, J. S.; Harrity, J. P.; Bonitaebus, P. J.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791-799
10. Ulman, R.; Grubbs, R. H. Organometallics 1998, 17, 2484-2489
11. Dias, E. L.; Nguyen, S. B.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3587-3897
12. Hérisson, J. L.; Chauvin, Y. Makromol. Chem. 1971, 141, 161-176
13. Stewart, I. C.; Benitez, D.; OLeary, D. J.; Tkatchouk, E.; Day, M. W.; Goddard, W. A., III; Grubbs, R. H. J. Am. Chem. Soc. 2009, 131, 10269-10278
14. Anderson, D. R.; OLeary, D. J.; Grubbs, R. H. Chem.-Eur. J. 2008, 14, 7536-7544
15. Anderson, D. R.; Hickstein, D. D.; OLeary, D. J.; Grubbs, R. H. J. Am. Chem. Soc. 2006, 128, 8386-8387
16. van der Eide, E. F.; Piers, W. E. Nat. Chem. 2010, 2, 571-576
17. van der Eide, E. F.; Romero, P. E.; Piers, W. E. J. Am. Chem. Soc. 2008, 130, 4485-4491
18. Romero, P. E.; Piers, W. E. J. Am. Chem. Soc. 2007, 129, 1698-1704
19. Wenzel, A. G.; Grubbs, R. H. J. Am. Chem. Soc. 2006, 128, 16048-16049
20. Romero, P. E.; Piers, W. E. J. Am. Chem. Soc. 2005, 127, 5032-5033
21. Trnka, T. M.; Day, M. W.; Grubbs, R. H. Organometallics 2001, 20, 3845-3847
22. Sanford, M. S.; Henling, L. M.; Day, M. W.; Grubbs, R. H. Angew. Chem., Int. Ed. 2000, 39, 3451-3453
23. Tallarico, J. A.; Bonitatebus, P. J.; Snapper, M. L. J. Am. Chem. Soc. 1997, 119, 7157-7158
24. Benitez, D.; Tkatchouk, E.; Goddard, W. A. Organometallics 2009, 28, 2643-2645
25. Benitez, D.; Tkatchouk, E.; Goddard, W. A., III. Chem. Commun. 2008, 6194-6196
26. Rowley, C. N.; van der Eide, E. F.; Piers, W. E.; Woo, T. K. Organometallics 2008, 27, 6043-6045
27. Naumov, S.; Buchmeiser, M. R. J. Phys. Org. Chem. 2008, 21, 963-970
28. Correa, A.; Cavallo, L. J. Am. Chem. Soc. 2006, 128, 13352-13353
29. Benitez, D.; Goddard, W. A., III. J. Am. Chem. Soc. 2005, 127, 12218-12219
30. Straub, B. F. Angew. Chem., Int. Ed. 2005, 44, 5974-5978
31. Suresh, C. H.; Baik, M.-H. J. Chem. Soc., Dalton Trans. 2005, 2982-2984
32. Suresh, C. H.; Koga, N. Organometallics 2004, 23, 76-80
33. Adlhart, C.; Chen, P. J. Am. Chem. Soc. 2004, 126, 3496-3510
34. Cavallo, L. J. Am. Chem. Soc. 2002, 124, 8965-8973
35. Carlson, R. G.; Gile, M. A.; Heppert, J. A.; Mason, M. H.; Powell, D. R.; Vander Velde, D.; Vilain, J. M. J. Am. Chem. Soc. 2002, 124, 1580-1581
36. Love, J. A.; Morgan, J. P.; Trnka, T. M.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 4035-4037
37. Dichloro[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene] (benzylidene)bis(3-bromopyridine)ruthenium(II) (4b) is commercially available from Sigma-Aldrich: item 682330 ($60/100 mg, 12/26/2010).
38. Hong, S. H.; Wenzel, A. G.; Salguero, T. T.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2007, 129, 7961-7968
39. Janse van Rensburg, W.; Steynberg, P. J.; Meyer, W. H.; Kirk, M. M.; Forman, G. S. J. Am. Chem. Soc. 2004, 126, 14332-14333
40. Blanc, F.; Berthoud, R.; Copéret, C.; Lesage, A.; Emsley, L.; Singh, R.; Kreickmann, T.; Schrock, R. R. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 12123-12127
41. Jiang, A. J.; Simpson, J. H.; Müller, P.; Schrock, R. R. J. Am. Chem. Soc. 2009, 131, 7770-7780
42. Flook, M. M.; Jiang, A. J.; Schrock, R. R.; Müller, P.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 7962-7963
43. Meinhart, J. D.; Anslyn, E. V.; Grubbs, R. H. Organometallics 1989, 8, 583-589
44. Hawkins, J. M.; Grubbs, R. H. J. Am. Chem. Soc. 1988, 110, 2821-2823
45. Howard, T. R.; Lee, J. B.; Grubbs, R. H. J. Am. Chem. Soc. 1980, 102, 6878-6880
46. For a discussion on the role of agostic interactions in the inhibition of decomposition in catalytic cycles, see: Harvey, B. G.; Mayne, C. L.; Arif, A. M.; Ernst, R. D. J. Am. Chem. Soc. 2005, 127, 16426-16435
47. Grubbs, R. H.; Coates, G. W. Acc. Chem. Res. 1996, 29, 85-93
48. Piers, W. E.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 9406-9407
49. Detailed spectral information can be found in the Experimental Section and Supporting Information.
50. Feldman, J.; Schrock, R. R. Prog. Inorg. Chem. 1991, 39, 1-6
51. Lee, L.-S.; Ou, H.-J.; Hsu, H.-L. Fluid Phase Equilib. 2005, 231, 221-230
52. Neuhaus, D.; Williamson, M. P. The Nuclear Overhauser Effect in Structural and Conformational Analysis, 2 nd ed.; Wiley-VCH: New York, 2000; pp 185 - 187.
53. Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935-967
54. Ramachandran, R.; Knight, C. T. G.; Kirkpatrick, R. J.; Oldfield, E. J. Magn. Reson. 1985, 65, 136-141
55. The EXSYCALC software package and instructions for crosspeak analysis can be obtained, free of charge, at: http://www.mestrelab.com.
56. Keitz, B. K.; Grubbs, R. H. Organometallics 2010, 29, 403-408
57. Sliwa, P.; Handzlik, J. Chem. Phys. Lett. 2010, 493, 273-278
58. Wenzel, A. G.; Chatterjee, A. K.; Grubbs, R. H. Olefin Cross-Metathesis In Comprehensive Organometallic Chemistry III: Review of the Literature 1993-2005; Ojima, I.; Hiyama, T., Eds.; Elsevier Ltd.: Oxford, U.K., 2006; Vol. 11.
59. Chatterjee, A. K. Olefin Cross-Metathesis In Handbook of Metathesis, 1 st ed.; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2002; Vol. 2, pp 246 - 295.
60. Zhao, X.; Ivanova, N.; Hadzovic, A.; Zimmer-De Iuliis, M.; Lough, A. J.; Morris, R. H. Organometallics 2008, 27, 503-508
61. Czelusniak, I.; Heywood, J. D.; Kenwright, A. M.; Khosravi, E. J. Mol. Catal. A: Chem. 2008, 280, 29-34
62. Kuhn, P.; Semeril, D.; Matt, D.; Chetcuti, M. J.; Lutz, P. Dalton Trans. 2007, 515-528
63. Qihui, C.; Yu, J.; Huang, J. Organometallics 2007, 26, 617-625
64. Bailey, P. J.; Melchionna, M.; Parsons, S. Organometallics 2007, 26, 128-135
65. Frieman, B. A. I. Advances in Heterogeneous Nickel-Catalyzed Reactions. II. Copper (I) Chloride as a Quick and Efficient Phosphine Scavenger. III Advances in Copper Hydride Chemistry Ph.D. Thesis, University of California, Santa Barbara, Santa Barbara, CA, 2006.
66. Krause, J. O.; Lubbad, S.; Nuyken, O.; Buchmeiser, M. R. Adv. Synth. Catal. 2003, 8, 996-1004
67. Nichiporuk, R. V.; Medniknov, E. G.; Dahl, L. F. J. Chem. Soc., Dalton Trans. 2002, 4116-4127
68. Connon, S. J.; Dunne, A. M.; Blechert, S. Angew. Chem., Int. Ed. 2002, 41, 3835-3838
69. Wang, C.; Friedrich, S.; Younkin, T. R.; Li, R. T.; Grubbs, R. H.; Bansleben, D. A.; Day, M. W. Organometallics 1998, 17, 3149-3151
70. Van der Velden, J. W. A.; Bour, J. J.; Bosman, W. P.; Noordik, J. H. J. Chem. Soc., Chem. Commun. 1981, 1218-1219
71. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 121, 8168-8179
72. The silica-bound toluenesulfonic acid (0.67 mmol/g) used in this experiment was purchased from Silicycle: www.silicycle.com; item R60530B-10G.