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A photoinduced reaction of perfluoroalkyl halides with 1,3-diarylprop-2-yn-1-ones catalyzed by DABSO

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Abstract

The sulfur dioxide surrogate of DABCO·(SO2)2 is used as an efficient catalyst for the cleavage of the perfluoroalkyl-halogen bond under visible-light irradiation for the first time. This unexpected reaction of perfluoroalkyl halides and 1,3-diarylprop-2-yn-1-ones catalyzed by DABCO·(SO2)2 in the presence of visible light proceeds smoothly, leading to 3-fluorinated indenones in good yields. During the reaction process, the cleavage of the perfluoroalkyl-halogen bond and subsequent radical oxidative cyclization are involved under metal-free conditions. A broad reaction scope is observed. Moreover, a plausible mechanism supported by theoretical calculations is proposed.

Graphical abstract: A photoinduced reaction of perfluoroalkyl halides with 1,3-diarylprop-2-yn-1-ones catalyzed by DABSO

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Publication details

The article was received on 10 Apr 2017, accepted on 29 May 2017 and first published on 31 May 2017


Article type: Research Article
DOI: 10.1039/C7QO00279C
Citation: Org. Chem. Front., 2017, Advance Article
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    A photoinduced reaction of perfluoroalkyl halides with 1,3-diarylprop-2-yn-1-ones catalyzed by DABSO

    Y. Li, Y. Lu, R. Mao, Z. Li and J. Wu, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00279C

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