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Issue 13, 2018
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Iron-catalyzed ortho trifluoromethylation of anilines via picolinamide assisted photoinduced C–H functionalization

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Abstract

A convenient, oxidant-free protocol was developed for the ortho trifluoromethylation of aniline via picolinamide assisted Fe-promoted C–H functionalization under ultraviolet irradiation. In this transformation acetone essentially acted as both a solvent to dissolve reactants and a low-cost radical initiator to efficiently generate a CF3 radical from Langlois’ reagent. A broad substrate scope was tolerated and picolinamide bearing strong electron withdrawing groups also could be transformed into the corresponding products with acceptable yields. Furthermore, the value of this method has been highlighted via the efficient synthesis of the nonsteroidal anti-inflammatory drug floctafenine.

Graphical abstract: Iron-catalyzed ortho trifluoromethylation of anilines via picolinamide assisted photoinduced C–H functionalization

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Publication details

The article was received on 28 Feb 2018, accepted on 05 Mar 2018 and first published on 05 Mar 2018


Article type: Communication
DOI: 10.1039/C8OB00511G
Citation: Org. Biomol. Chem., 2018,16, 2214-2218
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    Iron-catalyzed ortho trifluoromethylation of anilines via picolinamide assisted photoinduced C–H functionalization

    C. Xia, K. Wang, G. Wang and G. Duan, Org. Biomol. Chem., 2018, 16, 2214
    DOI: 10.1039/C8OB00511G

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