铜（0）催化的二硫化试剂与（杂）芳基/烷基卤化物的还原偶联反应
Copper(0)-Catalyzed Reductive Coupling of Disulfurating Reagents and (Hetero)aryl/Alkyl Halides.
作者信息
Chen Wang, Xu Jiuwen, Rao Weidong, Shen Shu-Su, Yang Zhao-Ying, Ackermann Lutz, Wang Shun-Yi
机构信息
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, China.
Key Laboratory of Biomass-Based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.
出版信息
Org Lett. 2024 Sep 18. doi: 10.1021/acs.orglett.4c03032.
Herein, we reported a copper(0)-catalyzed reductive coupling of disulfurating reagents and (hetero)aryl/alkyl halides. Copper(0) can be directly inserted into tetrasulfide and then undergoes reductive coupling with (hetero)aryl Iodides to construct disulfide. The method features the unprecedented use of copper(0)-catalyzed disulfurating reagents (tetrasulfides) in cross-coupling chemistry and is convenient with broad substrate scopes, even applicable to different halogenated hydrocarbons. It is worth noting that the methodology is practical with the late-stage modification of bioactive scaffolds of pharmaceuticals. In the meantime, the synthesis of disulfides is successfully achieved on a gram scale, indicating the approach is highly valuable.
在此，我们报道了一种铜（0）催化的二硫化试剂与（杂）芳基/烷基卤化物的还原偶联反应。铜（0）可直接插入四硫化物中，然后与（杂）芳基碘化物发生还原偶联以构建二硫化物。该方法的特点是在交叉偶联化学中前所未有的使用了铜（0）催化的二硫化试剂（四硫化物），并且操作方便，底物范围广泛，甚至适用于不同的卤代烃。值得注意的是，该方法对于药物生物活性支架的后期修饰具有实用性。同时，二硫化物的合成成功地实现了克级规模，表明该方法具有很高的价值。
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