Application of Bifunctional 2-Amino-1,4-naphthoquinones in Visible-Light-Promoted Photocatalyst-Free Alkene Perfluoroalkyl-Alkenylation

A simple and practical photochemical strategy for intermolecular perfluoroalkyl-alkenylation of alkenes with 2-amino-1,4-naphthoquinones and perfluoroalkyl iodides has been demonstrated under visible-light irradiation. Mechanistic studies reveal that easily available 2-amino-1,4-naphthoquinone subst...

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Veröffentlicht in:Organic letters 2021-01, Vol.23 (2), p.519-524
Hauptverfasser: Tang, Lin, Yang, Fang, Yang, Zhen, Chen, Hanfei, Cheng, Hao, Zhang, Shuaifei, Zhou, Qiuju, Rao, Weihao
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Sprache:eng
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Zusammenfassung:A simple and practical photochemical strategy for intermolecular perfluoroalkyl-alkenylation of alkenes with 2-amino-1,4-naphthoquinones and perfluoroalkyl iodides has been demonstrated under visible-light irradiation. Mechanistic studies reveal that easily available 2-amino-1,4-naphthoquinone substrates can serve as efficient photosensitizers to activate perfluoroalkyl iodides through a photoredox process. Therefore, the developed radical relay reaction proceeds smoothly without additional transition metals and photo-catalysts.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c04036