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Issue 8, 2016

Synthesis of trifluoromethylated 3,4-dihydroquinolin-2(1H)-ones via a photo-induced radical cyclization of benzene-tethered 1,7-enynes with Togni reagent

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Abstract

A photoinduced radical cyclization of benzene-tethered 1,7-enynes with Togni reagent in the presence of sodium iodide is developed. Under ultraviolet irradiation, (Z)-4-(iodomethylene)-3-(2,2,2-trifluoroethyl)-3,4-dihydroquinolin-2(1H)-ones are generated in moderate to good yields. The transformation works well without any metals or photo-redox catalysts at room temperature. During the reaction process, the reaction proceeds through a trifluoromethyl radical-triggered α,β-conjugated addition/intramolecular 6-exo cyclization/iodination, with the formation of multiple bonds. Good functional group tolerance is observed under the reaction conditions.

Graphical abstract: Synthesis of trifluoromethylated 3,4-dihydroquinolin-2(1H)-ones via a photo-induced radical cyclization of benzene-tethered 1,7-enynes with Togni reagent

Supplementary files

Article information


Submitted
14 Jun 2016
Accepted
21 Jun 2016
First published
22 Jun 2016

Org. Chem. Front., 2016,3, 994-998
Article type
Research Article

Synthesis of trifluoromethylated 3,4-dihydroquinolin-2(1H)-ones via a photo-induced radical cyclization of benzene-tethered 1,7-enynes with Togni reagent

Y. An, Y. Kuang and J. Wu, Org. Chem. Front., 2016, 3, 994 DOI: 10.1039/C6QO00267F

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