2,2,2-Trifluoroethanol-mediated hydroarylation of fluorinated alkynes with indoles: Application to diindolylmethanes
ARCHIV DER PHARMAZIE(2022)
Abstract
A new mild and practically simple alkyne hydroarylation protocol for the synthesis of 3-(indol-3-yl)-3-(trifluoromethyl)acrylic acid esters by the reaction of indole derivatives with ethyl/methyl 4,4,4-trifluoro-3-(indol-3-yl)but-2-enoates in trifluoroethanol was developed. This method has the following advantages: no catalyst, atom economy, high yields, broad substrate scope, and large-scale synthesis. The potential application of this protocol was further demonstrated by the synthesis of a variety of CF3-substituted synthons and a new class of (un)symmetrical 3,3MODIFIER LETTER PRIME-diindolylmethanes with a quaternary carbon core that might be biologically active.
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Key words
3-(indol-3-yl)-3-(trifluoromethyl)acrylic acid esters, C3-funtionalization of indole, diindolylmethanes, hydroarylation, indoles
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