Photoinduced Trifluoromethylselenolation of Aryl Halides with [Me4N][SeCF3]

A visible-light-induced metal-free trifluoromethylselenolation of aryl iodides and bromides with [Me4N]­[SeCF3] is described. The reaction was conducted at ambient temperature by successfully harnessing the light-sensitive SeCF3 reagent. Mechanistically, the EDA complexes between aryl halide and the...

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Veröffentlicht in:Organic letters 2023-11, Vol.25 (43), p.7884-7889
Hauptverfasser: Li, Fei, Han, Xue, Xu, Ziang, Zhang, Cheng-Pan
Format: Artikel
Sprache:eng
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Zusammenfassung:A visible-light-induced metal-free trifluoromethylselenolation of aryl iodides and bromides with [Me4N]­[SeCF3] is described. The reaction was conducted at ambient temperature by successfully harnessing the light-sensitive SeCF3 reagent. Mechanistically, the EDA complexes between aryl halide and the −SeCF3 anion or the base might be formed and excited by light, which subsequently undergo intracomplex SET processes to generate aryl and •SeCF3 radicals as key intermediates, allowing a convenient and green access to various aryl trifluoromethyl selenoethers.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03116