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Issue 34, 2016
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5-Position-selective C–H trifluoromethylation of 8-aminoquinoline derivatives

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We developed a copper-catalyzed 5-position-selective C–H trifluoromethylation of 8-aminoquinoline derivatives. The reaction proceeded with high functional group tolerance under mild conditions. In the case of quinolines with an amide, carbamate, urea, or sulfonamide group at the 8-position of quinoline moieties, a radical scavenger experiment indicated that the reaction proceeded via a radical pathway. The protecting group of an 8-amidoquinoline derivative could be removed by hydrolysis. On the other hand, the trifluoromethylation of 8-aminoquinolines was also promoted by other Lewis acids as well as a copper catalyst and proceeded even in the presence of a radical scavenger. These results indicated that the trifluoromethylation of 8-aminoquinolines proceeded via a Friedel–Crafts-type reaction. Interestingly, the copper salt works as either a catalyst for the formation of a CF3 radical or a Lewis acid to promote a Friedel–Crafts-type reaction, depending on the substrate.

Graphical abstract: 5-Position-selective C–H trifluoromethylation of 8-aminoquinoline derivatives

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The article was received on 20 Jun 2016, accepted on 01 Aug 2016 and first published on 01 Aug 2016

Article type: Paper
DOI: 10.1039/C6OB01325B
Citation: Org. Biomol. Chem., 2016,14, 8092-8100
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    5-Position-selective C–H trifluoromethylation of 8-aminoquinoline derivatives

    Y. Kuninobu, M. Nishi and M. Kanai, Org. Biomol. Chem., 2016, 14, 8092
    DOI: 10.1039/C6OB01325B

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