Menu
Home
People
Places
Arts
History
Plants & Animals
Science
Life & Culture
Technology
Reference.org
Radical fluorination
open-in-new
<p>Radical fluorination is a type of <a href="/facts/Fluorination/vYrGVWcJ">fluorination</a> reaction, complementary to nucleophilic and <a href="/facts/Electrophilic_fluorination/jWLsPWab">electrophilic</a> approaches. It involves the reaction of an independently generated carbon-centered <a href="/facts/Radical_(chemistry)/qFymuVoT">radical</a> with an atomic fluorine source and yields an <a href="/facts/Organofluorine_compound/EwWmHflJ">organofluorine compound</a>. </p> <p>Historically, only three atomic fluorine sources were available for radical fluorination: Fluorine (F2), <a href="/facts/Trifluoromethyl_hypofluorite/hJqyRJTF">hypofluorites</a> (O–F based reagents) and <a href="/facts/Xenon_difluoride/vKS7zojD">XeF2</a>. Their high reactivity, and the difficult handling of F2 and the hypofluorites, limited the development of radical fluorination compared to <a href="/facts/Electrophilic_fluorination/jWLsPWab">electrophilic</a> and nucleophilic methods. The uncovering of the ability of electrophilic N–F fluorinating agents to act as an atomic fluorine source led to a renaissance in radical fluorination. </p><p>Various methodologies have since been developed for the radical formation of C–F bonds. The radical intermediates have been generated from carboxylic acids and boronic acid derivatives, by radical addition to alkenes, or C–H and C–C bond activations. New sources of atomic fluorine are now emerging, such as metal fluoride complexes. </p>