Ruthenium-Catalyzed Olefin Cross-Metathesis with Tetrafluoroethylene and Analogous Fluoroolefins

Journal of the American Chemical Society

Volumn 137, Issue 22, 2015, Pages 7031-7034

  Takahira, Yusuke ^a   Morizawa, Yoshitomi ^a  

^a ASAHI GLASS CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE CONTAINING POLYMERS;

CATALYTIC TRANSFORMATION; MEDICINAL CHEMISTRY; OLEFIN CROSS-METATHESIS; ORGANIC SYNTHESIS; PARTIALLY FLUORINATED; POLYMER INDUSTRIES; TETRAFLUOROETHYLENE; THERMODYNAMICALLY STABLE;

OLEFINS;

ALKENE; ALKENE DERIVATIVE; FLUOROOLEFIN DERIVATIVE; RUTHENIUM; TETRAFLUOROETHYLENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; DENSITY FUNCTIONAL THEORY; MASS SPECTROMETRY; RING OPENING METATHESIS POLYMERIZATION; STOICHIOMETRY; SYNTHESIS;

EID: 84935854440     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b03342     Document Type: Article

References (33)

1. Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003.
2. Olefin Metathesis: Theory and Practice; Grela, K., Ed.; John Wiley & Sons: Hoboken, NJ, 2014.
3. Fustero, S.; Simón-Fuentes, A.; Barrio, P.; Haufe, G. Chem. Rev. 2015, 115, 871 - 930 and references therein
4. Macnaughtan, M. L.; Johnson, M. J. A.; Kampf, J. W. Organometallics 2007, 26, 780 - 782
5. Macnaughtan, M. L.; Gary, J. B.; Gerlach, D. L.; Johnson, M. J. A.; Kampf, J. W. Organometallics 2009, 28, 2880 - 2887
6. Macnaughtan, M. L. Ph.D. dissertation, University of Michigan, Ann Arbor, MI, 2009.
7. Trnka, T. M.; Day, M. W.; Grubbs, R. H. Angew. Chem., Int. Ed. 2001, 40, 3441 - 3444
8. Trnka, T. M. Ph.D. dissertation, California Institute of Technology, Pasadena, CA, 2003.
9. Fomine, S.; Ortega, J. V.; Tlenkopatchev, M. A. J. Mol. Catal. A: Chem. 2007, 263, 121 - 127
10. Fomine, S.; Tlenkopatchev, M. A. Appl. Catal., A 2009, 355, 148 - 155
11. Vasiliu, M.; Arduengo, A. J., III; Dixon, D. A. J. Phys. Chem. C 2014, 118, 13563 - 13577
12. A number of successes with α,ω-diene, one carbon-carbon double bond of which bears a fluorine atom, indicated certain compatibility for ring-closing metathesis; see ref 3 and references therein.
13. Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Wiley-VCH: Weinheim, Germany, 2004.
14. Chambers, R. D. Fluorine in Organic Chemistry; Blackwell: Oxford, U.K., 2004.
15. Uneyama, K. Organofluorine Chemistry; Blackwell: Oxford, U.K., 2006.
16. Ohashi, M.; Kambara, T.; Hatanaka, T.; Saijo, H.; Doi, R.; Ogoshi, S. J. Am. Chem. Soc. 2011, 133, 3256 - 3259
17. Ohashi, M.; Saijo, H.; Shibata, M.; Ogoshi, S. Eur. J. Org. Chem. 2013, 443 - 447
18. Saijo, H.; Sakaguchi, H.; Ohashi, M.; Ogoshi, S. Organometallics 2014, 33, 3669 - 3672
19. Ohashi, M.; Ogoshi, S. Catalysts 2014, 4, 321 - 345
20. Karel, K. J.; Tulip, T. H.; Ittel, S. D. Organometallics 1990, 9, 1276 - 1282
21. Cobalt complexes: Harrison, D. J.; Lee, G. M.; Leclerc, M. C.; Korobkov, I.; Baker, R. T. J. Am. Chem. Soc. 2013, 135, 18296 - 18299
22. Xu, L.; Solowey, D. P.; Vicic, D. A. Organometallics 2015, DOI: 10.1021/acs.organomet.5b00045
23. The term "Fischer carbene" refers to a metal complex bearing a divalent carbene ligand featuring at least one α-heteroatom substitutent (e.g., halogen atom, -OR, -SR, or -NR2) with lone-pair electrons.
24. Louie, J.; Grubbs, R. H. Organometallics 2002, 21, 2153 - 2164
25. Likewise, Macnaughtan has proposed a similar system involving interconversion between acetoxycarbene and other Fischer carbenes in her Ph.D. dissertation; see ref 4c.
26. Sashuk, V.; Samojłowicz, C.; Szadkowska, A.; Grela, K. Chem. Commun. 2008, 2468 - 2470
27. We have separately confirmed that catalytic cross-metathesis between enol ether and VdF actually occurred; see eqs. S1 and S2 in the Supporting Information.
28. Yang, Q.; Njardarson, J. T. Tetrahedron Lett. 2013, 54, 7080 - 7082
29. Only (E)- and (Z)- 4Ba were inseparable chromatographically; see the Supporting Information.
30. For compound characterization data, see the Supporting Information.
31. Nickel, A.; Ung, T.; Mkrtumyan, G.; Uy, J.; Lee, C. W.; Stoianova, D.; Papazian, J.; Wei, W.-H.; Mallari, A.; Schrodi, Y.; Pederson, R. L. Top. Catal. 2012, 55, 518 - 523
32. Authentic NMR data for 5Ac in C6D6 have not been reported previously, and we hence tentatively determined the formation by NMR and HRMS analyses of the reaction mixture, see the Supporting Information for details.
33. Benbrahim-Tallaa, L.; Lauby-Secretan, B.; Loomis, D.; Guyton, K. Z.; Grosse, Y.; El Ghissassi, F.; Bouvard, V.; Guha, N.; Mattock, H.; Straif, K. Lancet Oncol. 2014, 15, 924 - 925