Iron-catalyzed electrochemical C–H perfluoroalkylation of arenes

Mikhail Khrizanforov; Sofia Strekalova; Vera Khrizanforova; Valeriya Grinenko; Kirill Kholin; Marsil Kadirov; Timur Burganov; Aidar Gubaidullin; Tatyana Gryaznova; Oleg Sinyashin; Long Xu; David A. Vicic; Yulia Budnikova

doi:10.1039/C5DT03009A

Iron-catalyzed electrochemical C–H perfluoroalkylation of arenes†

Mikhail Khrizanforov,^a Sofia Strekalova,^a Vera Khrizanforova,^a Valeriya Grinenko,^a Kirill Kholin,^a Marsil Kadirov,^a Timur Burganov,^a Aidar Gubaidullin,^a Tatyana Gryaznova,^a Oleg Sinyashin,^a Long Xu,^b David A. Vicic^b and Yulia Budnikova*^a

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^a A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center of Russian Academy of Sciences, 8, Arbuzov str., 420088 Kazan, Russian Federation
E-mail: yulia@iopc.ru
Fax: +7843 2732253
Tel: +7843 2795335

^b Department of Chemistry, Lehigh University, 6 East Packer Avenue, Bethlehem, Pennsylvania 18015, USA

Abstract

A new iron-catalyzed reaction for the coupling of perfluoroalkyl iodides (R_FI) with aromatic substrates is described. The perfluoroalkylated arene products are obtained in good to excellent yields in the presence of a [(bpy)Fe(II)] catalyst (10%) electrochemically regenerated or generated from [(bpy)Fe(III)] at room temperature. The development, scope, and preliminary mechanistic studies of these transformations are reported.

This article is part of the themed collection: Fluorine

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Iron-catalyzed electrochemical C–H perfluoroalkylation of arenes†

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Iron-catalyzed electrochemical C–H perfluoroalkylation of arenes

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