Organofluorine Chemistry

The fluorine atom is by far the most electronegative element of the periodic table. Incorporation of fluorine atom(s) in organic molecules leads to a modification of a large range of properties including conformation, acid/base and hydrogen bond properties, lipophilicity, stability against oxidative and hydrolytic degradation. Fluorination of bioactive molecules and of organic materials is extensively used in property optimisation processes. It is estimated that up to 25% of current pharmaceuticals contain at least one fluorine atom, including many blockbusters. The incorporation of an ever-increasing list of fluorinated substitution motifs is an area of extensive current activity. In this respect, reagentless and flow techniques are of great interest.

Key Abstracts

Reducing the Lipophilicity of Perfluoroalkyl Groups by CF2–F/CF2–Me or CF3/CHExchange

Jeffries, B., Wang, Z., Graton, J., Holland, S. D., Brind, T., Greenwood, R. D. R., Le Questel, J.-Y., Scott, J. S., Chiarparin, E., and Linclau, B., J. Med. Chem. 2018, 61, 10602-10618

Investigating the Influence of (Deoxy)fluorination on the Lipophilicity of Non‐UV‐Active Fluorinated Alkanols and Carbohydrates by a New log P Determination Method

Linclau, B., Wang, Z., Compain, G., Paumelle, V., Fontenelle, C. Q., Wells, N., and Weymouth-Wilson, A., Angew. Chem. Int. Ed. Engl., 2016, 55, 674-678 

Minimising Conformational Bias in Fluoroprolines Through Vicinal Difluorination

Hofman, G. J., Ottoy, E., Light, M. E., Kieffer, B., Kuprov, I., Martins, J. C., Sinnaeve, D., and Linclau, B., Chem. Commun. 2018, 54, 5118-5121

Synthesis of fluorinated agonist of sphingosine-1-phosphate receptor 1

Aliouane, L., Chao, S., Brizuela, L., Pfund, E., Cuvillier, O., Jean, L., Renard, P.-Y., Lequeux, T.Bioorg. & Med. Chem. 2014, 22, 4955-4960

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