Tetrahedron p. 4431 - 4444 (1989)
Update date:2022-08-05
Topics:
Laurent, Eliane
Marquet, Bernard
Tardivel, Robert
Anodic oxidation of benzylic compounds 1 using CH3CN as a solvent and Et3N,3HF as a fluorinating reagent allowed to introduce a fluorine atom in α position of electron withdrawing group via carbocation 1+ (ECBECN mechanism).Whatever the E group, monofluorides 2 are obtained in good yields from paramethoxy derivatives 1 (R=p-OCH3).In this case, by raising the potential of working electrode after the monofluorination step, gem difluorides 3 can be directly prepared from 1.When the substituent of the phenyl ring is different of a methoxy group, a mixture of fluoride 2 and acetamide 4 is generally obtained and the ratio of these two compounds is related to cation stability.
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(1970)