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However, isoperfluoropropylated compounds remain largely underexplored, presumably due to the lack of efficient access to these compounds. Herein, we disclose the practical and efficient isoperfluoropropylation of aromatic C-H bonds through the invention of a hypervalent-iodine-based reagent-PFPI reagent, that proceeds via a Ag-X coupling process. The activation of the PFPI reagent without any catalysts or additives was demonstrated in the synthesis of isoperfluoropropylated electron-rich heterocycles, while its activity under photoredox catalysis was shown in the synthesis of isoperfluoropropylated non-activated arenes. Detailed mechanistic experiments and DFT calculations revealed a SET-induced concerted mechanistic pathway in the photoredox reactions. In addition, the unique conformation of <jats:italic>i<\/jats:italic>-C<jats:sub>3<\/jats:sub>F<jats:sub>7<\/jats:sub> in products, that involved intramolecular hydrogen bond was investigated by X-ray single-crystal diffraction and variable-temperature NMR experiments.<\/jats:p>","DOI":"10.1038\/s42004-023-00986-3","type":"journal-article","created":{"date-parts":[[2023,8,24]],"date-time":"2023-08-24T10:03:10Z","timestamp":1692871390000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Direct electrophilic and radical isoperfluoropropylation with i-C3F7-Iodine(III) reagent (PFPI reagent)"],"prefix":"10.1038","volume":"6","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2091-7679","authenticated-orcid":false,"given":"Yaxing","family":"Wu","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yunchen","family":"Jiang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fei","family":"Wang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bin","family":"Wang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7644-0884","authenticated-orcid":false,"given":"Chao","family":"Chen","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2023,8,24]]},"reference":[{"key":"986_CR1","doi-asserted-by":"crossref","first-page":"764","DOI":"10.1038\/nrd1821","volume":"4","author":"DT Wong","year":"2005","unstructured":"Wong, D. 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