Electrochemical cleavage of aryl ethers promoted by sodium borohydride

Journal of Organic Chemistry

Volumn 79, Issue 21, 2014, Pages 10189-10195

  Wu, Wen Bin ^a   Huang, Jing Mei ^a,b  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^b Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

LIGNIN;

ARYL ETHER; BENZYL ETHERS; DIARYL ETHERS; HIGH YIELD; LIGNIN MODEL COMPOUND; REDUCTIVE CLEAVAGE; ROOM TEMPERATURE; SODIUM BORO HYDRIDES;

ETHERS;

ALKYL ARYL ETHER; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SODIUM BOROHYDRIDE; BORANE DERIVATIVE; ETHER DERIVATIVE; LIGNIN;

ARTICLE; CATALYST; CONTROLLED STUDY; COVALENT BOND; DECOMPOSITION; DEPOLYMERIZATION; ELECTROCHEMISTRY; ELECTROLYSIS; OXIDATION; REACTION ANALYSIS; ROOM TEMPERATURE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMICAL ANALYSIS;

BOROHYDRIDES; CATALYSIS; ELECTROCHEMICAL TECHNIQUES; ETHERS; LIGNIN; MOLECULAR STRUCTURE; PHENOLS;

EID: 84910000544     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5018537     Document Type: Article

References (48)

1. Stöcker, M. Angew. Chem., Int. Ed. 2008, 47, 9200-9211
2. Demirbas, A. Energy Convers. Manage. 2009, 50, 2239-2249
3. Serrano-Ruiz, J. C.; Dumesic, J. A. Energy Environ. Sci. 2011, 4, 83-99
4. Tuck, C. O.; Pérez, E.; Horváth, I. T.; Sheldon, R. A.; Poliakoff, M. Science 2012, 337, 695-699
5. Huber, G. W.; Corma, A. Angew. Chem., Int. Ed. 2007, 46, 7184-7201
6. Zakzeski, J.; Bruijnincx, P. C. A.; Jongerius, A. L.; Weckhuysen, B. M. Chem. Rev. 2010, 110, 3552-3599
7. Azadi, P.; Inderwildi, O. R.; Farnood, R.; King, D. A. Renewable Sustainable Energy Rev. 2013, 21, 506-523
8. Sanderson, K. Nature 2011, 474, S12-S14
9. Barta, K.; Ford, P. C. Acc. Chem. Res. 2014, 47, 1503-1512
10. Ragauskas, A. J.; Beckham, G. T.; Biddy, M. J.; Chandra, R.; Chen, F.; Davis, M. F.; Davison, B. H.; Dixon, R. A.; Gilna, P.; Keller, M.; Langan, P.; Naskar, A. K.; Saddler, J. N.; Tschaplinski, T. J.; Tuskan, G. A.; Wyman, C. E. Science 2014, 344, 1246843
11. Kleine, T.; Buendia, J.; Bolm, C. Green Chem. 2013, 15, 160-166
12. Parthasarathi, R.; Romero, R. A.; Redondo, A.; Gnanakaran, S. J. Phys. Chem. Lett. 2011, 2, 2660-2666
13. He, J.; Zhao, C.; Lercher, J. A. J. Am. Chem. Soc. 2012, 134, 20768-20775
14. álvarez-Bercedo, P.; Martin, R. J. Am. Chem. Soc. 2010, 132, 17352-17353
15. Tobisu, M.; Yamakawa, K.; Shimasaki, T.; Chatani, N. Chem. Commun. 2011, 47, 2946-2948
16. Sergeev, A. G.; Hartwig, J. F. Science 2011, 332, 439-443
17. Sergeev, A. G.; Webb, J. D.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 20226-20229
18. Zaheer, M.; Hermannsdörfer, J.; Kretschmer, W. P.; Motz, G.; Kempe, R. ChemCatChem 2014, 6, 91-95
19. He, J.; Zhao, C.; Mei, D.; Lercher, J. A. J. Catal. 2014, 309, 280-290
20. Ren, Y.; Yan, M.; Wang, J.; Zhang, Z. C.; Yao, K. Angew. Chem., Int. Ed. 2013, 52, 12674-12678
21. Fedorov, A.; Toutov, A. A.; Swisher, N. A.; Grubbs, R. H. Chem. Sci. 2013, 4, 1640-1645
22. Maercker, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 972-989
23. Furukawa, J.; Omura, K.; Yamamoto, O.; Ishikawa, K. J. Chem. Soc., Chem. Commun. 1974, 77-78
24. Morrow, G. W. In Organic Electrochemistry, 4 th ed.; Lund, H.; Hammerich, O., Eds.; Marcel Dekker: New York, 2001.
25. Moeller, K. D. Tetrahedron 2000, 56, 9527-9554
26. Sperry, J. B.; Wright, D. L. Chem. Soc. Rev. 2006, 35, 605-621
27. Yoshida, J.; Kataoka, K.; Horcajada, R.; Nagaki, A. Chem. Rev. 2008, 108, 2265-2299
28. Frontana-Uribe, B. A.; Little, R. D.; Ibanez, J. G.; Palma, A.; Vasquez-Medrano, R. Green Chem. 2010, 12, 2099-2119
29. Hilt, G.; Smolko, K. I. Angew. Chem., Int. Ed. 2001, 40, 3399-3402
30. Hilt, G. Angew. Chem., Int. Ed. 2003, 42, 1720-1721
31. Nguyen, B. H.; Redden, A.; Moeller, K. D. Green Chem. 2014, 16, 69-72
32. Kirste, A.; Elsler, B.; Schnakenburg, G.; Waldvogel, S. R. J. Am. Chem. Soc. 2012, 134, 3571-3576
33. Elsler, B.; Schollmeyer, D.; Dyballa, K. M.; Franke, R.; Waldvogel, S. R. Angew. Chem., Int. Ed. 2014, 53, 5210-5213
34. Pacut, R. I.; Kariv-Miller, E. J. Org. Chem. 1986, 51, 3468-3470
35. Janissek, P. R.; Pardini, V. L.; Viertler, H. J. Chem. Soc., Chem. Commun. 1987, 576-577
36. Dabo, P.; Cyr, A.; Lessard, J.; Brossard, L.; Ménard, H. Can. J. Chem. 1999, 77, 1225-1229
37. Koppang, M. D.; Woolsey, N. F.; Bartak, D. E. J. Am. Chem. Soc. 1984, 106, 2799-2805
38. Koppang, M. D.; Woolsey, N. F.; Bartak, D. E. J. Am. Chem. Soc. 1985, 107, 4692-4700
39. Thornton, T. A.; Woolsey, N. F.; Bartak, D. E. J. Am. Chem. Soc. 1986, 108, 6497-6502
40. Thornton, T. A.; Ross, G. A.; Patil, D.; Mukaida, K.; Warwick, J. O.; Woolsey, N. F.; Bartak, D. E. J. Am. Chem. Soc. 1989, 111, 2434-2440
41. Huang, J.-M.; Wang, X.-X.; Dong, Y. Angew. Chem., Int. Ed. 2011, 50, 924-927
42. Huang, J.-M.; Lin, Z.-Q.; Chen, D.-S. Org. Lett. 2012, 14, 22-25
43. Qi, H.-L.; Chen, D.-S.; Ye, J.-S.; Huang, J.-M. J. Org. Chem. 2013, 78, 7482-7487
44. Barltrop, J. A.; Bradbury, D. J. Am. Chem. Soc. 1973, 95, 5085-5086
45. Deuterium incorporation was determined by using a developed Microsoft Excel program, see the supporting information of Young, K. J. H.; Meier, S. K.; Gonzales, J. M.; Oxgaard, J.; Goddard, W. A., III; Periana, R. A. Organometallics 2006, 25, 4734-4737
46. Bartoli, G.; Bosco, M.; Carlone, A.; Dalpozzo, R.; Locatelli, M.; Melchiorre, P.; Sambri, L. J. Org. Chem. 2006, 71, 9580-9588
47. Coutts, I. G. C.; Humphreys, D. J.; Schofield, K. J. Chem. Soc. C 1969, 1982-1986
48. Louafi, F.; Hurvois, J.-P.; Chibani, A.; Roisnel, T. J. Org. Chem. 2010, 75, 5721-5724