Direct Hydroxylation of Benzene to Phenol Using Hydrogen Peroxide Catalyzed by Nickel Complexes Supported by Pyridylalkylamine Ligands

Journal of the American Chemical Society

Volumn 137, Issue 18, 2015, Pages 5867-5870

  Morimoto, Yuma ^a   Bunno, Shuji ^a   Fujieda, Nobutaka ^a   Sugimoto, Hideki ^a   Itoh, Shinobu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; HYDROXYLATION; ISOTOPES; NICKEL; PHENOLS;

BENZENE HYDROXYLATION; CATALYTIC AMOUNTS; DIRECT HYDROXYLATION; HYDROXYLATION OF BENZENE; KINETIC ISOTOPE EFFECTS; MOLECULAR CATALYSTS; REACTION MECHANISM; TURNOVER NUMBER;

BENZENE;

BENZENE; CRESOL; HYDROGEN PEROXIDE; NICKEL COMPLEX; OXIDIZING AGENT; PHENOL; PYRIDYLALKYLAMINE LIGAND; UNCLASSIFIED DRUG; AMINE; LIGAND; NICKEL; ORGANOMETALLIC COMPOUND; PHENOL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; HYDROXYLATION; TEMPERATURE MEASUREMENT; CHEMISTRY; SYNTHESIS;

AMINES; BENZENE; CATALYSIS; HYDROGEN PEROXIDE; HYDROXYLATION; LIGANDS; MOLECULAR STRUCTURE; NICKEL; ORGANOMETALLIC COMPOUNDS; PHENOLS;

EID: 84929376720     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b01814     Document Type: Article

References (53)

1. Weber, M.; Weber, M.; Kleine-Boymann, M. In Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim, Germany, 2000.
2. Schmidt, R. J. Appl. Catal., A 2005, 280, 89 - 103
3. Mimoun, H.; Saussine, L.; Daire, E.; Postel, M.; Fischer, J.; Weiss, R. J. Am. Chem. Soc. 1983, 105, 3101 - 3110
4. Kimura, E.; Machida, R. J. Chem. Soc., Chem. Commun. 1984, 499 - 500
5. Hata, E.; Takai, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1994, 1849 - 1852
6. Bianchi, D.; Bortolo, R.; Tassinari, R.; Ricci, M.; Vignola, R. Angew. Chem., Int. Ed. 2000, 39, 4321 - 4323
7. Niwa, S.-i.; Eswaramoorthy, M.; Nair, J.; Raj, A.; Itoh, N.; Shoji, H.; Namba, T.; Mizukami, F. Science 2002, 295, 105 - 107
8. Tani, M.; Sakamoto, T.; Mita, S.; Sakaguchi, S.; Ishii, Y. Angew. Chem., Int. Ed. 2005, 44, 2586 - 2588
9. Dong, T.; Li, J.; Huang, F.; Wang, L.; Tu, J.; Torimoto, Y.; Sadakata, M.; Li, Q. Chem. Commun. 2005, 2724 - 2726
10. Tang, Y.; Zhang, J. Transition Met. Chem. 2006, 31, 299 - 305
11. Thibon, A.; Bartoli, J.-F.; Guillot, R.; Sainton, J.; Martinho, M.; Mansuy, D.; Banse, F. J. Mol. Catal. A: Chem. 2008, 287, 115 - 120
12. Conde, A.; Diaz-Requejo, M. M.; Perez, P. J. Chem. Commun. 2011, 47, 8154 - 8156
13. Shoji, O.; Kunimatsu, T.; Kawakami, N.; Watanabe, Y. Angew. Chem., Int. Ed. 2013, 52, 6606 - 6610
14. Shul'pin, G. B.; Kozlov, Y. N.; Shul'pina, L. S.; Carvalho, W. A.; Mandelli, D. RSC Adv. 2013, 3, 15065 - 15074
15. Raba, A.; Cokoja, M.; Herrmann, W. A.; Kuhn, F. E. Chem. Commun. 2014, 50, 11454 - 11457
16. Sheldon, R. A.; Kochi, J. K. In Metal-Catalyzed Oxidations of Organic Compounds; Sheldon, R. A.; Kochi, J. K., Eds.; Academic Press: New York, 1981; pp 315 - 339.
17. Catalytic Oxidations with Hydrogen Peroxide as Oxidant; Strukul, G., Ed.; Springer: Dordrecht, The Netherlands, 1992.
18. Haggin, J. Chem. Eng. News 1993, 71 (22) 23 - 27
19. Cruse, R. W.; Kaderli, S.; Karlin, K. D.; Zuberbuehler, A. D. J. Am. Chem. Soc. 1988, 110, 6882 - 6883
20. Nasir, M. S.; Cohen, B. I.; Karlin, K. D. J. Am. Chem. Soc. 1992, 114, 2482 - 2494
21. Karlin, K. D.; Nasir, M. S.; Cohen, B. I.; Cruse, R. W.; Kaderli, S.; Zuberbuehler, A. D. J. Am. Chem. Soc. 1994, 116, 1324 - 1336
22. Holland, P. L.; Rodgers, K. R.; Tolman, W. B. Angew. Chem., Int. Ed. 1999, 38, 1139 - 1142
23. Honda, K.; Cho, J.; Matsumoto, T.; Roh, J.; Furutachi, H.; Tosha, T.; Kubo, M.; Fujinami, S.; Ogura, T.; Kitagawa, T.; Suzuki, M. Angew. Chem., Int. Ed. 2009, 48, 3304 - 3307
24. Kunishita, A.; Doi, Y.; Kubo, M.; Ogura, T.; Sugimoto, H.; Itoh, S. Inorg. Chem. 2009, 48, 4997 - 5004
25. Tano, T.; Doi, Y.; Inosako, M.; Kunishita, A.; Kubo, M.; Ishimaru, H.; Ogura, T.; Sugimoto, H.; Itoh, S. Bull. Chem. Soc. Jpn. 2010, 83, 530 - 538
26. Que, J. L.; Tolman, W. B. Angew. Chem., Int. Ed. 2002, 41, 1114 - 1137
27. Mirica, L. M.; Ottenwaelder, X.; Stack, T. D. P. Chem. Rev. 2004, 104, 1013 - 1046
28. Lewis, E. A.; Tolman, W. B. Chem. Rev. 2004, 104, 1047 - 1076
29. Suzuki, M. Acc. Chem. Res. 2007, 40, 609 - 617
30. Itoh, S.; Bandoh, H.; Nagatomo, S.; Kitagawa, T.; Fukuzumi, S. J. Am. Chem. Soc. 1999, 121, 8945 - 8946
31. Nagataki, T.; Ishii, K.; Tachi, Y.; Itoh, S. Dalton Trans. 2007, 1120 - 1128
32. The conversion of benzene was not identical to the yield because of evaporation of benzene (∼10% in 5 h). This was confirmed by a blank experiment.
33. A large part of the H2O2 (44%) remained after the reaction.
34. For catalyst 3, we observed ligand hydroxylation at the benzylic position of the phenethyl arm in about 10% yield by 1H NMR analysis, whereas we did not detect such a ligand-hydroxylated product with catalyst 2. For details, see the SI.
35. Cho, J.; Sarangi, R.; Annaraj, J.; Kim, S. Y.; Kubo, M.; Ogura, T.; Solomon, E. I.; Nam, W. Nat. Chem. 2009, 1, 568 - 572
36. Kieber-Emmons, M. T.; Annaraj, J.; Seo, M. S.; Van Heuvelen, K. M.; Tosha, T.; Kitagawa, T.; Brunold, T. C.; Nam, W.; Riordan, C. G. J. Am. Chem. Soc. 2006, 128, 14230 - 14231
37. The concentrations of benzene, H2O2, and TEA were optimized (see Table S2).
38. After the reaction, 4.3 mmol of H2O2 (17% of the initial amount) remained.
39. Luo, Y.-R. Comprehensive Handbook of Chemical Bond Energies; CRC Press: Boca Raton, FL, 2007.
40. Kamata, K.; Yamaura, T.; Mizuno, N. Angew. Chem., Int. Ed. 2012, 51, 7275 - 7278
41. In aromatic oxygenation reactions, a shift of the deuteron on the attacked carbon to the neighboring carbon (a so-called NIH shift) is often observed. In this system, however, the NIH shift was not observed in the oxygenation reaction of toluene-4- d 1. For details, see Scheme S4.
42. Augusti, R.; Dias, A. O.; Rocha, L. L.; Lago, R. M. J. Phys. Chem. A 1998, 102, 10723 - 10727
43. Emmert, M. H.; Cook, A. K.; Xie, Y. J.; Sanford, M. S. Angew. Chem., Int. Ed. 2011, 50, 9409 - 9412
44. Ohkubo, K.; Kobayashi, T.; Fukuzumi, S. Angew. Chem., Int. Ed. 2011, 50, 8652 - 8655
45. Unfortunately, we could not detect any spectral change upon addition of H2O2 to a solution of catalyst 2 at low temperature (below -60 C), under which conditions catalyst 3, supported by the less hindered bepa ligand, generates a dinickel(III) bis(μ-oxo) species (see ref 30).
46. Shiren, K.; Ogo, S.; Fujinami, S.; Hayashi, H.; Suzuki, M.; Uehara, A.; Watanabe, Y.; Moro-oka, Y. J. Am. Chem. Soc. 2000, 122, 254 - 262
47. Cho, J.; Furutachi, H.; Fujinami, S.; Tosha, T.; Ohtsu, H.; Ikeda, O.; Suzuki, A.; Nomura, M.; Uruga, T.; Tanida, H.; Kawai, T.; Tanaka, K.; Kitagawa, T.; Suzuki, M. Inorg. Chem. 2006, 45, 2873 - 2885
48. Hikichi, S.; Yoshizawa, M.; Sasakura, Y.; Komatsuzaki, H.; Moro-oka, Y.; Akita, M. Chem.-Eur. J. 2001, 7, 5011 - 5028
49. Itoh, S.; Bandoh, H.; Nakagawa, M.; Nagatomo, S.; Kitagawa, T.; Karlin, K. D.; Fukuzumi, S. J. Am. Chem. Soc. 2001, 123, 11168 - 11178
50. Cho, J.; Sarangi, R.; Nam, W. Acc. Chem. Res. 2012, 45, 1321 - 1330
51. 14-tmc has also been reported to be able to stabilize dinickel(II) peroxide species generated by the reaction between the corresponding Ni(I) complex and molecular oxygen (see ref 52).
52. Kieber-Emmons, M. T.; Schenker, R.; Yap, G. P. A.; Brunold, T. C.; Riordan, C. G. Angew. Chem., Int. Ed. 2004, 43, 6716 - 6718
53. The oxygenation efficiency of benzene derivatives with catalyst 2 was found to decrease upon the introduction of electron-donating substituents. This unusual selectivity of benzene oxygenation over phenol oxygenation may be due to this tendency.