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Updated: Dec 24, 2025

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Kinetics of Electrophilic Fluorination of Steroids and Epimerisation of Fluorosteroids
Neshat Rozatian1, Antal Harsanyi1, Ben J Murray1
1Chemistry Department, Durham University, South Road, Durham, DH1 3LE, UK.
Abstract:
Fluorinated steroids, which are synthesised by electrophilic fluorination, form a significant proportion of marketed pharmaceuticals. To gain quantitative information on fluorination at the 6-position of steroids, kinetics studies were conducted on enol ester derivatives of progesterone, testosterone, cholestenone and hydrocortisone with a series of electrophilic N-F reagents. The stereoselectivities of fluorination reactions of progesterone enol acetate and the kinetic effects of additives, including methanol and water, were investigated. The kinetics of epimerisation of 6β-fluoroprogesterone to the more pharmacologically active 6α-fluoroprogesterone isomer in HCl/acetic acid solutions are detailed.
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