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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| Published in: | Tetrahedron letters Vol. 59; no. 45; pp. 3999 - 4002 |
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| Main Authors: | , , , , |
| Format: | Journal Article |
| Language: | English |
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Elsevier Ltd
07-11-2018
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| Abstract | [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. |
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| AbstractList | [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. |
| Author | Griffin, Paul J. Fava, Matthew A. Whittaker, St. John T. Kolonko, Kristopher J. Catino, Arthur J. |
| Author_xml | – sequence: 1 givenname: Paul J. surname: Griffin fullname: Griffin, Paul J. organization: Department of Chemistry, The University of Scranton, Scranton, PA 18510, USA – sequence: 2 givenname: Matthew A. surname: Fava fullname: Fava, Matthew A. organization: Department of Chemistry, The University of Scranton, Scranton, PA 18510, USA – sequence: 3 givenname: St. John T. surname: Whittaker fullname: Whittaker, St. John T. organization: Department of Chemistry, The University of Scranton, Scranton, PA 18510, USA – sequence: 4 givenname: Kristopher J. surname: Kolonko fullname: Kolonko, Kristopher J. organization: Stewart’s Advanced Instrumentation and Technology (SAInT) Center, Siena College, Loudonville, NY 12211, USA – sequence: 5 givenname: Arthur J. orcidid: 0000-0002-9761-0360 surname: Catino fullname: Catino, Arthur J. email: arthur.catino@scranton.edu organization: Department of Chemistry, The University of Scranton, Scranton, PA 18510, USA |
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| Cites_doi | 10.1021/acs.chemrev.6b00439 10.1002/(SICI)1099-1395(199707)10:7<499::AID-POC896>3.0.CO;2-2 10.1021/la305069e 10.1021/ol4013052 10.1016/j.tetlet.2013.06.026 10.1038/ncomms14641 10.1016/j.tet.2014.06.104 10.1016/S0040-4039(97)00136-6 10.1021/cm0008056 10.1021/ja053689m 10.1002/adsc.200606068 10.1016/j.tet.2012.10.044 10.1021/ol061268j 10.1039/c2cc35758e 10.1038/nenergy.2017.8 10.1021/jo00061a011 10.1055/s-0036-1588563 10.1021/ol503213z 10.1002/adsc.201100931 10.1248/cpb.41.842 10.1021/ja2108992 |
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| Keywords | Tetraphenylmethane Friedel-Crafts cyclization desulfurization Tetraarylmethanes Bismuth catalysis |
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•Tetraarylmethanes prepared with all phenyl groups and diverse substitution.•Friedel-Crafts cyclization gives 9,9-diarylthioxanthene... |
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| SubjectTerms | Bismuth catalysis Friedel-Crafts cyclization desulfurization Tetraarylmethanes Tetraphenylmethane |
| Title | Synthesis of tetraarylmethanes via a Friedel-Crafts cyclization/desulfurization strategy |
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