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Diarylmethane synthesis through Re2O7-catalyzed bimolecular dehydrative Friedel–Crafts reactions

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Abstract

This manuscript describes the application of Re2O7 to the syntheses of diarylmethanes from benzylic alcohols through solvolysis followed by Friedel–Crafts alkylation. The reactions are characterized by broad substrate scope, low catalyst loadings, high chemical yields, and minimal waste generation. The intermediate perrhenate esters are superior leaving groups to chlorides and bromides in these reactions. The polarity and water sequestering capacity of hexafluoroisopropyl alcohol are critical to the success of these processes. Re2O7 is a precatalyst for HOReO3, which serves as a less costly and easily handled promoter for these reactions. Oxorhenium catalysts selectively activate alcohols in the presence of similarly substituted acetates, indicating a unique chemoselectivity and mechanism in comparison to Brønsted acid catalysis.

Graphical abstract: Diarylmethane synthesis through Re2O7-catalyzed bimolecular dehydrative Friedel–Crafts reactions

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Publication details

The article was received on 11 Aug 2018, accepted on 30 Aug 2018 and first published on 13 Sep 2018


Article type: Edge Article
DOI: 10.1039/C8SC03570A
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY license
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    Diarylmethane synthesis through Re2O7-catalyzed bimolecular dehydrative Friedel–Crafts reactions

    Q. Qin, Y. Xie and P. E. Floreancig, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C8SC03570A

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