Preparation of 2,2-difluoroenol silyl ethers by electroreductive defluorination of trifluoromethyl ketones

Tetrahedron Letters

Volumn 39, Issue 22, 1998, Pages 3741-3744

  Uneyama, Kenji ^a   Maeda, Kazushige ^a   Kato, Tsuyoshi ^a   Katagiri, Toshimasa ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINE DERIVATIVE; FLUOROFORM; KETONE DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DEFLUORINATION; ELECTROLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REDUCTION; SYNTHESIS;

EID: 0032575165     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00574-7     Document Type: Article

References (35)

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16. 6. (A) Base-catalyzed dehydrofluorination of 2,2,2-trifluoroethyl groups: Howarth, J. A.; Owton, W.M.; Percy, J. M.; Rock, M. K. Tetrahedron 1995, 51, 10289-10302. Shi, G.-Q.; Cao, Z.-Y.; Cai, W.-L. Tetrahedron 1995, 51, 5011-5018. Narita, T.; Hagiwara, T.; Hamana, H.; Tomooka, K.; Liu, Y.-Z.; Nakai, T. Tetrahedron Lett. 1995, 36, 6091-6094. Gimbert, Y.; Moradpour, A.; Dive, G.; Dehareng, D.; Lahlil, K. J. Org. Chem. 1993, 58, 4685-4690. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 1641-1644.
17. 6. (A) Base-catalyzed dehydrofluorination of 2,2,2-trifluoroethyl groups: Howarth, J. A.; Owton, W.M.; Percy, J. M.; Rock, M. K. Tetrahedron 1995, 51, 10289-10302. Shi, G.-Q.; Cao, Z.-Y.; Cai, W.-L. Tetrahedron 1995, 51, 5011-5018. Narita, T.; Hagiwara, T.; Hamana, H.; Tomooka, K.; Liu, Y.-Z.; Nakai, T. Tetrahedron Lett. 1995, 36, 6091-6094. Gimbert, Y.; Moradpour, A.; Dive, G.; Dehareng, D.; Lahlil, K. J. Org. Chem. 1993, 58, 4685-4690. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 1641-1644.
18. 6. (A) Base-catalyzed dehydrofluorination of 2,2,2-trifluoroethyl groups: Howarth, J. A.; Owton, W.M.; Percy, J. M.; Rock, M. K. Tetrahedron 1995, 51, 10289-10302. Shi, G.-Q.; Cao, Z.-Y.; Cai, W.-L. Tetrahedron 1995, 51, 5011-5018. Narita, T.; Hagiwara, T.; Hamana, H.; Tomooka, K.; Liu, Y.-Z.; Nakai, T. Tetrahedron Lett. 1995, 36, 6091-6094. Gimbert, Y.; Moradpour, A.; Dive, G.; Dehareng, D.; Lahlil, K. J. Org. Chem. 1993, 58, 4685-4690. Ichikawa, J.; Sonoda, T.; Kobayashi, H. Tetrahedron Lett. 1989, 30, 1641-1644.
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29. 9. For example, we have recently found that 1-substituted-2-trifluoromethylbenzimidazole (6) was easily defluorinated by electroreduction, but the product, 1-substituted-2-difluoromethylbenzimidazole (7) was also easily defluorinated because of its similar reduction potentials. So 6 and 7 were defluorinated competitively, producing 1-substituted-2-monofluoromethylbenzimidazole (8) as a by-product. When 4 F/mol electricity was passed, 6 (42 %, recovery of 6), 7 (37 %) and 8 (5 %) were produced, respectively.
30. 10. LUMO energies of 4, 5a (R=Ph) and difluoromethyl phenyl ketone (9) were -0.97 eV, -0.41 eV and -0.87 eV, respectively (calculated by PM3 geometry optimization of Mac Spartan Plus), suggesting different reducibility between 4 and 5a, and similar one between 4 and 9.
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35. 2 solution, which provided 2,2-difluoro-3-hydroxy-1,3-diphenyl-1-propanone [51% from 4 (R=Ph)]. The corresponding TES and TBDMS-enolates (5b and 5c) were isolable by silica gel column chromatography.