Hydrodefluorination of fluoroaromatics by isopropyl alcohol catalyzed by a ruthenium NHC complex. An unusual role of the carbene ligand

ACS Catalysis

Volumn 6, Issue 11, 2016, Pages 7956-7961

  Mai, Van Hung ^a   Nikonov, Georgii I ^a  

^a BROCK UNIVERSITY   (Canada)

Author keywords

Hydrodefluorination; Mechanism; N heterocyclic carbene; Ruthenium catalysis; Transfer hydrogenation

Indexed keywords

AROMATIC COMPOUNDS; CATALYSIS; FLUORINE COMPOUNDS; LIGANDS; MECHANISMS; SUBSTRATES;

BOND REDUCTIONS; HYDRODEFLUORINATION; ISOPROPYL ALCOHOLS; MECHANISM-BASED; N-HETEROCYCLIC CARBENES; REDUCING REAGENTS; RUTHENIUM CATALYSIS; TRANSFER HYDROGENATIONS;

RUTHENIUM COMPOUNDS;

EID: 85010855297     PISSN: None     EISSN: 21555435     Source Type: Journal    
DOI: 10.1021/acscatal.6b02004     Document Type: Article

References (58)

1. (a) Hiyama, T. Organofluorine Compounds: Chemistry and Applications; Springer: Berlin, 2000.
2. (b) Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity and Applications; Wiley: Hoboken, NJ, 2004.
3. (c) Jeschke, P. ChemBioChem 2004, 5, 570.
4. (d) Soloshonok, V. A. Fluorine-Containing Synthons; American Chemical Society: Washington, DC, 2005; ACS Symposium Series 911
5. . (e) Begue, J. P.; Bonnet-Delpon, D. J. Fluorine Chem. 2006, 127, 992.
6. (g) Nakajima, T.; Groult, H. Fluorinated Materials for Energy Conversion; Elsevier: Amsterdam, 2005.
7. (h) Banks, R. E.; Smart, B. E.; Tatlow, J. C. Organofluorine Chemistry: Principles and Commercial Applications; Springer: Berlin, 1994.
8. (i) Banks, R. E. Fluorine Chemistry at the Millennium: Fascinated by Fluorine; Elsevier: Amsterdam, 2000.
9. (j) Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
10. (a) Wang, J.; Sanchez-Rosello , M.; Aceña, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Chem. Rev. 2014, 114, 2432−2506.
11. (b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320−330.
12. (c) Thayer, A. M. Chem. Eng. News 2006, 84, 15−24.
13. (a) Campbell, M. G.; Ritter, T. Chem. Rev. 2015, 115, 612−633.
14. (b) Grushin, V. V. Acc. Chem. Res. 2010, 43, 160−171.
15. Lee, E.; Kamlet, A. S.; Powers, D. C.; Neumann, C. N.; Boursalian, G. B.; Furuya, T.; Choi, D. C.; Hooker, J. M.; Ritter, T. Science 2011, 334, 639−642.
16. Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2015, 54, 3216−3221.
17. (a) Ahrens, T.; Kohlmann, J.; Ahrens, M.; Braun, T. Chem. Rev. 2015, 115, 931−972.
18. (b) Kuehnel, M. F.; Lentz, D.; Braun, T. Angew. Chem., Int. Ed. 2013, 52, 3328−3348.
19. (c) Whittlesey, M. K.; Peris, E. ACS Catal. 2014, 4, 3152.
20. (d) Amii, H.; Uneyama, K. Chem. Rev. 2009, 109, 2119−2183.
21. (e) Hu, J.-Y.; Zhang, J.-L. Top. Organomet. Chem. 2015, 52, 143−196.
22. (a) Aizenberg, M.; Milstein, D. Science 1994, 265, 359−361.
23. (b) Vela, J.; Smith, J. M.; Yu, Y.; Ketterer, N. A.; Flaschenriem, C. J.; Lachicotte, R. J.; Holland, P. L. J. Am. Chem. Soc. 2005, 127, 7857.
24. (c) Peterson, A. A.; McNeill, K. Organometallics 2006, 25, 4938.
25. (d) Braun, T.; Wehmeier, F.; Altenhoener, K. Angew. Chem., Int. Ed. 2007, 46, 5321−5324.
26. (e) Reade, S. P.; Mahon, M. F.; Whittlesey, M. K. J. Am. Chem. Soc. 2009, 131, 1847−1861.
27. (f) Luehmann, N.; Panisch, R.; Müller, T. Appl. Organomet. Chem. 2010, 24, 533−537.
28. (g) Barrios-Francisco, R.; Benitez-Paez, T.; Flores-Alamo, M.; Arevalo, A.; Garcia, J. J. Chem. - Asian J. 2011, 6, 842.
29. (h) Ahrens, M.; Scholz, G.; Braun, T.; Kemnitz, E. Angew. Chem., Int. Ed. 2013, 52, 5328− 5332.
30. (i) Chen, Z.; He, C.-Y.; Yin, Z.; Chen, L.; He, Y.; Zhang, X. Angew. Chem., Int. Ed. 2013, 52, 5813−5817.
31. (j) Schwartsburd, L.; Mahon, M. F.; Poulten, R. C.; Warren, M. R.; Whittlesey, M. K. Organometallics 2014, 33, 6165−6170.
32. (k) Yamada, T.; Saito, K.; Akiyama, T. Adv. Synth. Catal. 2016, 358, 62−66.
33. (a) Douvris, C.; Ozerov, O. V. Science 2008, 321, 1188−1190.
34. (b) Caputo, C. B.; Stephan, D. W. Organometallics 2012, 31, 27−30.
35. (c) Caputo, C. B.; Hounjet, L. J.; Dobrovetsky, R.; Stephan, D. W. Science 2013, 341, 1374−1377.
36. (d) Zhu, J.; Perez, M.; Caputo, C. B.; Stephan, D. W. Angew. Chem., Int. Ed. 2016, 55, 1417−1421.
37. Schaub, T.; Backes, M.; Radius, U. J. Am. Chem. Soc. 2006, 128, 15964−15965.
38. Arevalo, A.; Tlahuext-Aca, A.; Flores-Alamo, M.; Garcia, J. J. J. Am. Chem. Soc. 2014, 136, 4634.
39. (a) Baumgartner, R.; McNeill, K. Environ. Sci. Technol. 2012, 46, 10199.
40. (b) Baumgartner, R.; Stieger, G. K.; McNeill, K. Environ. Sci. Technol. 2013, 47, 6545−6553.
41. (c) Braun, T.; Noveski, D.; Ahijado, M.; Wehmeier, F. Dalton Trans. 2007, 3820−3825.
42. (d) Stanger, K. J.; Angelici, R. J. J. Mol. Catal. A: Chem. 2004, 207, 59−68.
43. (e) Yang, H.; Gao, H. R.; Angelici, R. J. Organometallics 1999, 18, 2285−2287.
44. (f) Young, R. J.; Grushin, V. V. Organometallics 1999, 18, 294.
45. Wang, D.; Astruc, D. Chem. Rev. 2015, 115, 6621−6686.
46. For the use of sodium formate as the hydrogen source, see: Li, J.; Zheng, T.; Sun, H.; Li, X. Dalton Trans. 2013, 42, 13048−13053.
47. Kuhl, S.; Schneider, R.; Fort, Y. Adv. Synth. Catal. 2003, 345, 341−344.
48. Sawama, Y.; Yabe, Y.; Shigetsura, M.; Yamada, T.; Nagata, S.; Fujiwara, Y.; Maegawa, T.; Monguchi, Y.; Sajiki, H. Adv. Synth. Catal. 2012, 354, 777.
49. (a) Sabater, S.; Mata, J. A.; Peris, E. Organometallics 2015, 34, 1186.
50. (b) Sabater, S.; Mata, J. A.; Peris, E. Nat. Commun. 2013, 4, 2553.
51. Matsunami, A.; Kuwata, S.; Kayaki, Y. ACS Catal. 2016, 6, 5181−5185.
52. Mai, V. H.; Nikonov, G. I. Organometallics 2016, 35, 943−949.
53. Mai, V. H.; Nikonov, G. I.; Kuzmina, L. G.; Churakov, A. V.; Korobkov, I.; Howard, J. A. K. Dalton Trans 2016, 45, 208.
54. Macgregor, S. A.; McKay, D.; Panetier, J. A.; Whittlesey, M. K. Dalton Trans. 2013, 42, 7386−7395.
55. Johnson, S. A.; Hatnean, J. A.; Doster, M. E. Progress in Inorganic Chemistry; Wiley: Hoboken, NJ, 2011; p 255.
56. Belt, S. T.; Duckett, S. B.; Helliwell, M.; Perutz, R. N. J. Chem. Soc., Chem. Commun. 1989, 928−930.
57. Panetier, J. A.; Macgregor, S. A.; Whittlesey, M. K. Angew. Chem., Int. Ed. 2011, 50, 2783−2786.
58. Huang, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18 (12), 2370−2375.