Dimitri M. Khramov, Andrew J Boydston, C. Bielawski
Apr 4, 2006
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Organic letters
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.