Highly efficient synthesis and solid-state characterization of 1,2,4,5-tetrakis(alkyl- and arylamino)benzenes and cyclization to their respective benzobis(imidazolium) salts

Organic Letters
Dimitri M KhramovChristopher W Bielawski

Abstract

[reaction: see text] New synthetic methodology to a variety of 1,2,4,5-tetraaminobenzenes and their corresponding benzobis(imidazolium) salts has been accomplished. Palladium-catalyzed coupling of various 1,2,4,5-tetrabromo- or 1,2,4,5-tetrachlorobenzenes with aryl- or tert-alkylamines afforded the respective tetrakis(N-substituted)aminobenzenes in excellent yields. This enabled comparative solid-state structural analyses of this elusive class of electron-rich arenes with their oxidized derivatives. The tetraamines were found to undergo formylative cyclization to the corresponding benzobis(imidazolium) salts in good to excellent yields.

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Citations

Jan 18, 2011·Chemical Reviews·Laure BenhamouVincent César
Sep 6, 2013·Inorganic Chemistry·María AlfonsoPedro Molina
May 2, 2007·Chemical Society Reviews·Kyle A WilliamsChristopher W Bielawski
Jun 10, 2010·Chemical Communications : Chem Comm·Kyle A Williams, Christopher W Bielawski
Jan 26, 2007·Journal of the Royal Society, Interface·Kyle A WilliamsChristopher W Bielawski
Apr 19, 2016·Chemical Reviews·Karel GoossensKoen Binnemans
Mar 4, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Yannick BorguetLionel Delaude
Aug 23, 2006·Dalton Transactions : an International Journal of Inorganic Chemistry·Andrew J Boydston, Christopher W Bielawski
Aug 15, 2006·Angewandte Chemie·Dimitri M KhramovChristopher W Bielawski
Apr 10, 2008·Angewandte Chemie·F Ekkehardt Hahn, Mareike C Jahnke
May 8, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Christian RadloffRoland Fröhlich
Oct 15, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Sergei KrupskiF Ekkehardt Hahn
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May 8, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·C Daniel VarnadoChristopher W Bielawski
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Feb 15, 2008·Journal of the American Chemical Society·Andrew J BoydstonChristopher W Bielawski

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