Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Metal-Free Oxidative C–C Coupling of Arylamines Using a Quinone-Based Organic Oxidant

Metal-Free Oxidative C–C Coupling of Arylamines Using a Quinone-Based Organic Oxidant
Parthasarathy Venkatakrishnan, Sudesh Mallick, Sudhakar Maddala
A variety of arylamines are shown to undergo oxidative C–C bond formation using quinone-based chloranil/H+ reagent as the recyclable organic (metal-free) oxidant system to afford benzidines/naphthidines. Arylamines (3°/2°) designed with various substituents were employed to understand the steric as well as electronic preferences of oxidative dimerization, and a mechanism involving amine radical cation has been proposed. The tetraphenylbenzidine derivative obtained via oxidative C–C coupling has been further converted to blue-emissive hole-transporting material via a simple chemical transformation. This study highlights the preparation of novel HTMs in a simple, economic, and efficient manner.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01377

DOI: 10.1021/acs.joc.7b01377

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