Huang Yubing, Li Xianwei, Wang Xu, Yu Yue, Zheng Jia, Wu Wanqing, Jiang Huanfeng
Key Laboratory of Functional Molecular Engineering of Guangdong Province , School of Chemistry and Chemical Engineering , South China University of Technology , Guangzhou 510640 , China . Email:
Chem Sci. 2017 Oct 1;8(10):7047-7051. doi: 10.1039/c7sc02867a. Epub 2017 Aug 15.
Sulfur-containing nitriles have important research value in the life sciences due to their diverse biological activities resulting from the sulfur and cyano functional groups. Herein, a copper-catalyzed cyanothiolation of -tosylhydrazones with thiocyanates to generate α-arylthioalkanenitriles bearing sulfur-substituted quaternary carbon center atoms has been described. This novel protocol involves the procedure of copper carbene species promoting S-CN bond cleavage and C-CN/C-S bond reconstruction to introduce both sulfur and cyano groups onto a single carbon center. This cyanothiolation reaction will greatly enhance the synthetic utility of carbenoid species as new entries for the construction of diverse heteroatom-containing nitriles cyanofunctionalization of metal-carbene species.
含硫腈类化合物因其硫和氰基官能团具有多样的生物活性，在生命科学领域具有重要的研究价值。本文描述了一种铜催化的对甲苯磺酰腙与硫氰酸盐的氰硫基化反应，以生成带有硫取代季碳中心原子的α-芳硫基链烷腈。这种新颖的方法涉及铜卡宾物种促进S-CN键断裂以及C-CN/C-S键重构的过程，从而将硫和氰基引入到同一个碳中心上。这种氰硫基化反应将极大地提高类卡宾物种作为构建多样含杂原子腈类化合物新方法的合成效用，即金属卡宾物种的氰基官能化。
