biostudies-literatureCorti VMinistero dell?Istruzione, dell?Universit? e della RicercaUniversit? degli Studi di TriesteAXA Research FundPON ricerca e innovazioneRegione Autonoma Friuli Venezia GiuliaConsorzio Interuniversitario Nazionale per la Scienza e Tecnologia dei Materiali6008-6016https://www.ebi.ac.uk/biostudies/studies/S-EPMC10167682biostudies-literatureUnknown88(9)A light-driven protocol for the synthesis of 2,3-dihydrobenzofurans under mild conditions is reported. Specifically, the cascade process is initiated by the photochemical activity of allyl-functionalized phenolate anions, generated <i>in situ</i> upon deprotonation of the corresponding phenols. The reaction proceeds rapidly with reaction times as low as 35 min, delivering a wide range of densely functionalized products (20 examples, yields up to 69%). Mechanistic studies have also been performed providing convincing evidence for the photochemical formation of carbon-centered radical species. A cascade reaction pathway involving a tandem atom transfer radical addition (ATRA) and an intramolecular nucleophilic substitution (SN) process is proposed to occur.The Journal of organic chemistryPhotoinduced Cascade Reactions of 2-Allylphenol Derivatives toward the Production of 2,3-Dihydrobenzofurans.PMC101676822017PBXPN4ART. 4LR 2/2011FRA2022Dosso JCorti VFilippini GPrato MfalsePhotoinduced Cascade Reactions of 2-Allylphenol Derivatives toward the Production of 2,3-Dihydrobenzofurans.A light-driven protocol for the synthesis of 2,3-dihydrobenzofurans under mild conditions is reported. Specifically, the cascade process is initiated by the photochemical activity of allyl-functionalized phenolate anions, generated <i>in situ</i> upon deprotonation of the corresponding phenols. The reaction proceeds rapidly with reaction times as low as 35 min, delivering a wide range of densely functionalized products (20 examples, yields up to 69%). Mechanistic studies have also been performed providing convincing evidence for the photochemical formation of carbon-centered radical species. A cascade reaction pathway involving a tandem atom transfer radical addition (ATRA) and an intramolecular nucleophilic substitution (SN) process is proposed to occur.2023-01-01T00:00:00Z2023 May2025-04-22T00:33:25.952Z2025-04-05T19:36:49.064ZS-EPMC101676823700101710.1021/acs.joc.3c00347