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- Bielawski, Christopher W.
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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
- Author(s)
- Khramov, DM, Boydston, AJ, Bielawski, CW
- Issued Date
- 2006-04
- Citation
- ORGANIC LETTERS, v.8, no.9, pp.1831 - 1834
- Abstract
- 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.
- Publisher
- AMER CHEMICAL SOC
- ISSN
- 1523-7060
- Keyword
- BUILDING-BLOCKS, ARYL HALIDES, CATALYZED SYNTHESIS, COMPLEXES, ARYLAMINES, CARBENE, QUINONE
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