Synthesis of tetraarylmethanes via a Friedel-Crafts cyclization/desulfurization strategy

[Display omitted] •Tetraarylmethanes prepared with all phenyl groups and diverse substitution.•Friedel-Crafts cyclization gives 9,9-diarylthioxanthene precursors.•Tetraarylmethanes obtained by desulfurization with Raney nickel.•Tetraarylmethanes with electron-withdrawing or electron-donating groups....

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Bibliographic Details
Published in:	Tetrahedron letters Vol. 59; no. 45; pp. 3999 - 4002
Main Authors:	Griffin, Paul J., Fava, Matthew A., Whittaker, St. John T., Kolonko, Kristopher J., Catino, Arthur J.
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 07-11-2018
Subjects:	Bismuth catalysis Friedel-Crafts cyclization desulfurization Tetraarylmethanes Tetraphenylmethane Tetraphenylmethane Friedel-Crafts cyclization desulfurization Tetraarylmethanes Bismuth catalysis
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Summary:	[Display omitted] •Tetraarylmethanes prepared with all phenyl groups and diverse substitution.•Friedel-Crafts cyclization gives 9,9-diarylthioxanthene precursors.•Tetraarylmethanes obtained by desulfurization with Raney nickel.•Tetraarylmethanes with electron-withdrawing or electron-donating groups.•Nucleophilic addition to benzophenone to form triarylmethanols. Tetraarylmethanes are an important class of molecules that contain four aryl groups bonded to a central carbon atom. The shape/three-dimensionality of these molecules makes them suitable for organic light-emitting diodes (OLEDs), organic solar cells, hydrogen storage, and even drug-delivery. Despite their importance, there are only a few methods available for their preparation. Herein, we report a simple procedure for the preparation of tetraarylmethanes that involves a bismuth-catalyzed Friedel-Crafts cyclization followed by a desulfurization reaction mediated by Raney nickel.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/j.tetlet.2018.09.056