Liu Jianming, Zhang Yanyan, Yue Yuanyuan, Wang Zhixian, Shao Huibin, Zhuo Kelei, Lv Qingzhang, Zhang Zhiguo
Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering , Henan Normal University , Xinxiang , Henan 453007 , P.R. China.
J Org Chem. 2019 Oct 18;84(20):12946-12959. doi: 10.1021/acs.joc.9b01586. Epub 2019 Aug 21.
We report a base-promoted metal-free approach for the synthesis of thieno[2,3-]indole derivatives. This method combined four C-H σ-bond cleavage reactions of two different kinds of C-H bonds and two C-S σ-bond formation processes. A series of thieno[2,3-]indoles were obtained starting from 3-benzylindole derivatives with good yields and high regioselectivity, with the elemental sulfur serving as a cheap and readily available sulfur source. Good efficiency could be maintained even when the reaction was performed on a gram scale. A plausible mechanism was proposed on the basis of mechanistic studies.
我们报道了一种碱促进的无金属方法来合成噻吩并[2,3-b]吲哚衍生物。该方法结合了两种不同类型C-H键的四个C-H σ键裂解反应和两个C-S σ键形成过程。从3-苄基吲哚衍生物出发，以元素硫作为廉价且易于获得的硫源，以良好的产率和高区域选择性获得了一系列噻吩并[2,3-b]吲哚。即使在克级规模上进行反应，也能保持良好的效率。基于机理研究提出了一个合理的机理。
