Department of Chemistry, Indian Institute of Technology Madras , Chennai 600 036, Tamil Nadu, India.
J Org Chem. 2017 Sep 1;82(17):8958-8972. doi: 10.1021/acs.joc.7b01377. Epub 2017 Aug 17.
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.
各种芳基胺被证明可以使用基于醌的氯苯并二恶嗪/H 试剂作为可回收的有机（无金属）氧化剂体系进行氧化 C-C 键形成，从而得到联苯/萘啶。设计具有各种取代基的芳基胺（3°/2°）用于了解氧化二聚化的空间和电子偏好，并提出了涉及胺自由基阳离子的机制。通过氧化 C-C 偶联获得的四苯基联苯二胺衍生物通过简单的化学转化进一步转化为蓝色发光空穴传输材料。这项研究强调了以简单、经济和有效的方式制备新型 HTM 的方法。
