Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis

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Publikace nespadá pod Filozofickou fakultu, ale pod Přírodovědeckou fakultu. Oficiální stránka publikace je na webu muni.cz.

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MEYER Andreas U. SLANINA Tomáš YAO Chang-Jiang KÖNIG Burkhard

Rok publikování 2016
Druh Článek v odborném periodiku
Časopis / Zdroj ACS Catalysis
Fakulta / Pracoviště MU

Přírodovědecká fakulta

Citace
www http://pubs.acs.org/doi/abs/10.1021/acscatal.5b02410
Doi http://dx.doi.org/10.1021/acscatal.5b02410
Obor Organická chemie
Klíčová slova perfluorophenyl; photocatalysis; visible light; metal-free conditions; C-H arylation; transient spectroscopy
Popis Visible light and eosin Y catalyze the direct arylation of simple arenes with fluorinated aryl bromides by a photoredox process. The reaction scope is broad in fluorinated compounds and arenes and the general and simple procedure provides a metal-free alternative for the synthesis of synthetically valuable polyfluorinated biaryl structures. The mild reaction conditions allow a selective reaction with the alkaloid brucine without protection of functional groups illustrating the potential of the process for late stage functionalization. Mechanistic investigations reveal the photoreduction of eosin Y via its triplet state by triethylamine and subsequent electron transfer from the eosin Y radical anion to the polyfluorinated bromoarene, which fragments into the polyfluorinated aryl radical and a bromide anion. A radical chain reaction mechanism was excluded by a quenching factor analysis.
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