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. 2023 Apr 19;28(8):3578.
doi: 10.3390/molecules28083578.

Silver-Promoted Radical Cascade Aryldifluoromethylation/Cyclization of 2-Allyloxybenzaldehydes for the Synthesis of 3-Aryldifluoromethyl-Containing Chroman-4-one Derivatives

Qianqian Sun  1 , Hongxiao Li  1 , Xingyu Chen  1 , Jian Hao  1 , Hongmei Deng  2 , Haizhen Jiang  1   3
Affiliations

Silver-Promoted Radical Cascade Aryldifluoromethylation/Cyclization of 2-Allyloxybenzaldehydes for the Synthesis of 3-Aryldifluoromethyl-Containing Chroman-4-one Derivatives

Qianqian Sun et al. Molecules. .

Abstract

A convenient silver-promoted radical cascade aryldifluoromethylation/cyclization of 2-allyloxybenzaldehydes has been developed. Experimental studies disclosed that the addition of aryldifluoromethyl radicals in situ produced from easily accessible gem-difluoroarylacetic acids to unactivated double bonds in 2-allyloxybenzaldehyde was an effective route to access a series of 3-aryldifluoromethyl-containing chroman-4-one derivatives in moderate to good yields under mild reaction conditions.

Keywords: aryldifluoromethylation/cyclization; chroman-4-one derivatives; radical cascade.

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Conflict of interest statement

The authors declare that they have no known competing financial interest or personal relationships that could have appeared to influence the work reported in this paper.

Figures

Figure 1
Figure 1
Examples of the bioactive compounds with a 3-substituent chroman-4-one moiety.
Scheme 1
Scheme 1
Synthesis of 3-difluoromethylene-containing chroman-4-one derivatives.
Figure 2
Figure 2
X-ray crystallography of 3aq′ (gray for carbon atoms, green for fluorine atom, yellow for sulfur atom and red for oxygen atom).
Scheme 2
Scheme 2
Control experiments.
Scheme 3
Scheme 3
Plausible reaction mechanism.
See this image and copyright information in PMC

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