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Synthesis of 2,3-dihydrobenzofurans via a photochemical gold-mediated atom transfer radical addition reaction

A light-mediated cyclization reaction initiated by an atom transfer radical addition (ATRA) of haloalkanes onto alkenes was exploited for the synthesis of functionalized dihydrobenzofurans. Initial investigation indicated that the dimeric gold catalyst [Au2(μ-dppm)2Cl2] can effectively be used for i...

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Hauptverfasser: Melder, Julian J. (VerfasserIn) , Witzel, Sina (VerfasserIn) , Terres, Sophia (VerfasserIn) , Bary, Philippe de (VerfasserIn) , Krohne, Lukas (VerfasserIn) , Rudolph, Matthias (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn)
Dokumenttyp: Article (Journal) Editorial
Sprache:Englisch
Veröffentlicht: June 28, 2024
In: Organic letters
Year: 2024, Jahrgang: 26, Heft: 27, Pages: 5664-5669
ISSN:1523-7052
DOI:10.1021/acs.orglett.4c01626
Online-Zugang:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.orglett.4c01626
Volltext
Verfasserangaben:Julian J. Melder, Sina Witzel, Sophia Terres, Philippe de Bary, Lukas Krohne, Matthias Rudolph, and A. Stephen K. Hashmi
Beschreibung
Zusammenfassung:A light-mediated cyclization reaction initiated by an atom transfer radical addition (ATRA) of haloalkanes onto alkenes was exploited for the synthesis of functionalized dihydrobenzofurans. Initial investigation indicated that the dimeric gold catalyst [Au2(μ-dppm)2Cl2] can effectively be used for intermolecular ATRA reactions. Further, the reactivity was applied in a cascade-like cyclization for the preparation of dihydrobenzofuran derivatives. With the presented photochemical approach, the functionalization can be achieved directly from ortho-allylphenols in yields of up to 96% under mild conditions.
Beschreibung:Gesehen am 13.12.2024
Beschreibung:Online Resource
ISSN:1523-7052
DOI:10.1021/acs.orglett.4c01626

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