Radical fluorination is a type of fluorination reaction, complementary to nucleophilic and electrophilic approaches.[1] It involves the reaction of an independently generated carbon-centered radical with an atomic fluorine source and yields an organofluorine compound.
Historically, only three atomic fluorine sources were available for radical fluorination: Fluorine (F2), hypofluorites (O–F based reagents) and XeF2. Their high reactivity, and the difficult handling of F2 and the hypofluorites, limited the development of radical fluorination compared to electrophilic and nucleophilic methods.[2] The uncovering of the ability of electrophilic N–F fluorinating agents to act as an atomic fluorine source[3] led to a renaissance in radical fluorination.[2]
Various methodologies have since been developed for the radical formation of C–F bonds.[1] 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.
^ abSibi, Mukund P.; Landais, Yannick (Feb 2013). "Csp3–F Bond Formation: A Free-Radical Approach". Angewandte Chemie International Edition. 52 (13): 3570–3572. doi:10.1002/anie.201209583. PMID 23441011.
^Rueda-Becerril, Montserrat; Chatalova-Sazepin, Claire; Leung, Joe C. T.; Okbinoglu, Tulin; Kennepohl, Pierre; Paquin, Jean-François; Sammis, Glenn M. (Mar 2012). "Fluorine Transfer to Alkyl Radicals". Journal of the American Chemical Society. 134 (9): 4026–4029. doi:10.1021/ja211679v. ISSN 0002-7863. PMID 22320293.
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