20259-36-3Relevant academic research and scientific papers
Decarboxylative fluorination of aliphatic carboxylic acids via photoredox catalysis
Ventre, Sandrine,Petronijevic, Filip R.,Macmillan, David W. C.
supporting information, p. 5654 - 5657 (2015/05/20)
The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO2-extrusion and F? transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental evidence indicates that an oxidative quenching pathway is operable in this broadly applicable fluorination protocol.
FLUORINATION OF CYCLOHEXANOLS WITH 4-MORPHOLINOSULFUR TRIFLUORIDE
Mange, Kevin C.,Middleton, W. J.
, p. 405 - 414 (2007/10/02)
In contrast to most simple alcohols, cyclohexanol has proved to be a surprisingly difficult compound to fluorinate with aminosulfur trifluorides.In the reaction of 4-morpholinosulfur trifluoride (morpho-DAST) with cyclohexanol, a correlation was found between the polarity index of the solvent, P', and the yield of fluorocyclohexane.In solvents of low polarity, there appears to be an uncharged intermediate that leads to fluorocyclohexane.In solvents of higher polarity, there appears to be a charged intermediate that gives fluorocyclohexane.By a study of the fluorination of cis- and trans-4-tert-butylcyclohexanol, conformational effects were shown to be a major factor in hindering the SN2 attack by fluoride ion on the reactive intermediate(s).
