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Metal-free visible-light-induced hydroxy-perfluoroalkylation of conjugated olefins using enamine catalyst.

ABSTRACT: We developed a simple and sustainable method for the hydroxy-perfluoroalkylation of electron-deficient conjugated olefins and styrenes. In this protcol, in situ generated enamine forms electron-donor-accepter (EDA) complexes with perfluoroalkyl iodide, and reaction proceed with visible-light irradiation. Tertiary amine also interacts with perfluoroalkyl iodide via halogen-bonding, promoting the perfluoroalkyl radical generation. This reaction does not require any transition-metal or photoredox catalyst, and gaseous oxygen is used as the green hydroxy source. Moreover, various commercially available substrates and perfluoroalkyl iodides were tolerated, affording the desired hydroxy-perfluoroalkylated products in good to moderate yields (>50 examples, up to 90%).

SUBMITTER: Tagami K

PROVIDER: S-EPMC9667149 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

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Metal-free visible-light-induced hydroxy-perfluoroalkylation of conjugated olefins using enamine catalyst.

Tagami Koto K Ofuji Yu Y Kanbara Tadashi T Yajima Tomoko T

RSC advances 20221115 51

We developed a simple and sustainable method for the hydroxy-perfluoroalkylation of electron-deficient conjugated olefins and styrenes. In this protcol, in situ generated enamine forms electron-donor-accepter (EDA) complexes with perfluoroalkyl iodide, and reaction proceed with visible-light irradiation. Tertiary amine also interacts with perfluoroalkyl iodide via halogen-bonding, promoting the perfluoroalkyl radical generation. This reaction does not require any transition-metal o ...[more]

PMID: 36425182

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