Electrochemical Oxidation of Organotrifluoroborate Compounds

ChemElectroChem

Volumn 3, Issue 12, 2016, Pages 2078-2083

  Suzuki, Junji ^a   Tanigawa, Masahiro ^a   Inagi, Shinsuke ^a   Fuchigami, Toshio ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

anodic acetoxylation; electrosynthesis; organoboronic acid esters; organotrifluoroborate; effect

Indexed keywords

ANODES; CYCLIC VOLTAMMETRY; ELECTROCHEMICAL OXIDATION; ELECTRODES; ESTERS; OXIDATION;

ACETOXYLATION; ELECTROCHEMICAL ANALYSIS; ELECTROSYNTHESIS; ORGANOBORONIC ACIDS; ORGANOTRIFLUOROBORATE; OXIDATION POTENTIALS; RADICAL COUPLING; THEORETICAL ASPECTS;

ANODIC OXIDATION;

EID: 84994850611     PISSN: None     EISSN: 21960216     Source Type: Journal    
DOI: 10.1002/celc.201600451     Document Type: Article

References (39)

1. A. Pelter, K. Smith, H. C. Brown, Borane Reagents, Academic Press, London, 1988.
2. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
3. X. Y. Liu, D. R. Bai, S. Wang, Angew. Chem. Int. Ed. 2006, 45, 5475;
4. Angew. Chem. 2006, 118, 5601.
5. M. Miyata, Y. Chujo, Polym. J. 2002, 34, 967.
6. T. Miyahara, K. Kurihara, J. Am. Chem. Soc. 2004, 126, 5684.
7. J. H. Morris, H. J. Gysling, D. Reed, Chem. Rev. 1985, 85, 51.
8. J. Yoshida, T. Nokami, S. Suga, in Organic Electrochemistry, 5th ed. (Eds.: O. Hammerich, B. Speiser), CRC Press, Boca Raton, FL, 2015, p. 1364.
9. T. Taguchi, M. Itoh, A. Suzuki, Chem. Lett. 1973, 2, 719.
10. T. Taguchi, Y. Takahashi, M. Itoh, A. Suzuki, Chem. Lett. 1974, 3, 1021.
11. Y. Takahashi, M. Tokuda, M. Itoh, A. Suzuki, Synthesis 1976, 616.
12. Y. Takahashi, M. Tokuda, M. Itoh, A. Suzuki, Chem. Lett. 1978, 7, 669.
13. H. Schäfer, D. Koch, Angew. Chem. 1972, 84, 32.
14. Y. Takahashi, M. Tokuda, M. Itoh, A. Suzuki, Chem. Lett. 1975, 4, 523.
15. Y. Takahashi, M. Tokuda, M. Itoh, A. Suzuki, Chem. Lett. 1977, 6, 999.
16. Y. Takahashi, M. Tokuda, M. Itoh, A. Suzuki, Chem. Lett. 1980, 9, 461.
17. A. A. Humffray, L. F. G. Williams, Chem. Commun. 1965, 616.
18. J. T. Keating, P. S. Skell, J. Org. Chem. 1969, 34, 1479.
19. A. A. Humffray, L. F. G. Williams, Electrochim. Acta 1972, 17, 401.
20. L. F. G. Williams, A. A. Humffray, Electrochim. Acta 1972, 17, 409.
21. D.-Q. Shi, A. Gitkis, J. Y. Becker, Electrochim. Acta 2007, 53, 1824.
22. I. M. Malkowsky, C. E. Rommel, R. Fröhlich, U. Griesbach, H. Pütter, S. R. Waldvogel, Chem. Eur. J. 2006, 12, 7482.
23. M. Tanigawa, Y. Kuriyama, S. Inagi, T. Fuchigami, Elecrichim. Acta 2016, 199, 314.
24. J. Suzuki, N. Shida, S. Inagi, T. Fuchigami, Electroanalysis, 2016 DOI: 10.1002/elan.201600130.
25. S. Darses, J.-P. Genet, Chem. Rev. 2008, 108, 288.
26. S. Darses, J.-P. Genet, Eur. J. Org. Chem. 2003, 4313.
27. G. Sorin, R. M. Malloquin, Y. Contie, A. Baralle, M. Malacria, J.-P. Goddard, L. Fensterbank, Angew. Chem. Int. Ed. 2010, 49, 8721;
28. Angew. Chem. 2010, 122, 8903.
29. G. A. Molander, V. Colombel, V. A. Braz, Org. Lett. 2011, 13, 1852.
30. Y. Yasu, T. Koike, M. Akita, Adv. Synth. Catal. 2012, 354, 3414.
31. K. Miyazawa, Y. Yasu, T. Koike, M. Akita, Chem. Commun. 2013, 49, 7249.
32. H. Huang, G. Zhang, L. Gong, S. Zhang, Y. Chen, J. Am. Chem. Soc. 2014, 136, 2280.
33. J. C. Tellis, D. N. Primer, G. A. Molander, Science 2014, 345, 433.
34. L. A. Shundrin, V. V. Bardin, H.-J. Frohn, Z. Anorg. Allg. Chem. 2004, 630, 1253.
35. J. Yoshida, K. Kataoka, R. Horcajada, A. Nagaki, Chem. Rev. 2008, 108, 2265.
36. J. J. Riehl, A. Fougerousse, Bull. Soc. Chim. Fr. 1968, 4083.
37. A. N. Thadani, R. A. Batey, Org. Lett. 2002, 4, 3827.
38. R. A. Batey, T. D. Quach, Tetrahedron Lett. 2001, 42, 9099.
39. F. Barba, M. G. Quintanilla, G. Montero, J. Org. Chem. 1995, 60, 5658.