Acid-Promoted Reaction of Trifluoromethylated Allyl Alcohols with Arenes. Stereoselective Synthesis of CF3-Alkenes and CF3-Indanes

The Journal of Organic Chemistry
Anna N KazakovaAleksander V Vasilyev

Abstract

Reaction of 4-aryl-1,1,1-trifluorobut-3-en-2-ols [CF3-allyl alcohols, ArCH═CHCH(OH)CF3] with arenes under activation with anhydrous FeCl3 or FSO3H was studied. We found that the transformation led to trifluoromethylated alkenes [Ar(Ar')CHCH═CHCF3] or 1-trifluoromethylated indanes (CF3-indanes). The formation of these two types of reaction products strongly depends on the nucleophilicity of the starting arene and the electrophilicity of cationic intermediates generated from CF3-allyl alcohols under reaction conditions. Benzene, anisole, veratrole, and ortho-xylene lead exclusively to CF3-alkenes with an E-configuration. More π-donating polymethylated arenes (pseudocumene, mesitylene) afford only CF3-indanes with a predominantly cis-orientation of substituents at positions 1 and 3 of the indane ring. Meta- and para-xylenes show an intermediate behavior; they may form both CF3-alkenes and/or CF3-indanes. The mechanisms of the investigated transformations are discussed.

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Citations

Feb 5, 2016·The Journal of Organic Chemistry·Steve SaulnierAleksander V Vasilyev
Mar 7, 2017·Organic & Biomolecular Chemistry·Matvei Yu MartynovAleksander V Vasilyev
Apr 9, 2021·Beilstein Journal of Organic Chemistry·Anthony J FernandesSébastien Thibaudeau

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