Photocatalytic/Cu-Promoted C−H Activations: Visible-light-Induced ortho-Selective Perfluoroalkylation of Benzamides

A visible‐light‐induced and copper‐promoted perfluoroalkylation of benzamides was successfully developed under the assistance of an 8‐aminoquinoline directing group. It provides a straightforward method for the synthesis of ortho‐perfluoroalkyl‐substituted benzoic acid derivatives. The reaction empl...

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Bibliographic Details
Published in:Chemistry : a European journal 2016-04, Vol.22 (18), p.6218-6222
Main Authors: Chen, Xiang, Tan, Ze, Gui, Qingwen, Hu, Liang, Liu, Jidan, Wu, Jing, Wang, Guangwei
Format: Article
Language:English
Subjects:
Activation
Benzamide
chelation-assisted
Chemistry
Cu-promoted
C−H activation
Derivatives
Dyes
Fluorescence
Light bulbs
Light-emitting diodes
perfluoroalkylation
photocatalysis
Synthesis
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Summary:A visible‐light‐induced and copper‐promoted perfluoroalkylation of benzamides was successfully developed under the assistance of an 8‐aminoquinoline directing group. It provides a straightforward method for the synthesis of ortho‐perfluoroalkyl‐substituted benzoic acid derivatives. The reaction employs a cheap organic dye eosin Y as the photoredox catalyst and is run under the irradiation of a 26 W fluorescent LED light bulb. Light up your chemistry! Synthesis of ortho‐perfluoroalkylated benzamides can be achieved by 8‐aminoquinoline‐directed copper‐promoted C−H activation under photoredox catalysis (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201600229