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A compilation of Functional Group Transfer Reagents and their diverse activation mechanisms leading to the release of radicals are discussed. The substrate scope for each radical is analyzed and classified into three categories according to the electronic properties of the substrates. Density functional theory computational analysis provides insights into the chemical reactivity of several fluorinated radicals through their electrophilicity and nucleophilicity parameters. Theoretical analysis of their reduction potentials also highlights the remarkable correlation between electrophilicity and oxidizing ability. It is also established that highly fluorinated radicals (e.g. \u22c5OCF\n                    <jats:sub>3<\/jats:sub>\n                    ) are capable of engaging in single\u2010electron transfer (SET) processes rather than radical addition, which is in good agreement with experimental literature data. A reactivity scale, based on activation barrier of addition of these radicals to benzene is also elaborated using the high accuracy DLPNO\u2010(U)CCSD(T) method.\n                  <\/jats:p>","DOI":"10.1002\/anie.202318377","type":"journal-article","created":{"date-parts":[[2024,1,28]],"date-time":"2024-01-28T22:20:17Z","timestamp":1706480417000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":78,"title":["Review and Theoretical Analysis of Fluorinated Radicals in Direct C\n                    <sub>Ar<\/sub>\n                    \u2212H Functionalization of (Hetero)arenes"],"prefix":"10.1002","volume":"63","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8372-7982","authenticated-orcid":false,"given":"Anthony J.","family":"Fernandes","sequence":"first","affiliation":[{"name":"Department f\u00fcr Chemie und Biochemie Universit\u00e4t Bern  Freiestrasse\u20053 3012 Bern Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3110-2125","authenticated-orcid":false,"given":"Rahul","family":"Giri","sequence":"additional","affiliation":[{"name":"Department f\u00fcr Chemie und Biochemie Universit\u00e4t Bern  Freiestrasse\u20053 3012 Bern Switzerland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8387-5261","authenticated-orcid":false,"given":"Kendall N.","family":"Houk","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biochemistry University of California  90095 Los Angeles California United States"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0131-1188","authenticated-orcid":false,"given":"Dmitry","family":"Katayev","sequence":"additional","affiliation":[{"name":"Department f\u00fcr Chemie und Biochemie Universit\u00e4t Bern  Freiestrasse\u20053 3012 Bern 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