Yuan Tingting, Chen Xiang-Yu, Ji Tengfei, Yue Huifeng, Murugesan Kathiravan, Rueping Magnus
KAUST Catalysis Center, KCC, King Abdullah University of Science and Technology, KAUST Thuwal 23955-6900 Saudi Arabia
Institute of Organic Chemistry, RWTH Aachen University Landoltweg 1 52074 Aachen Germany.
Chem Sci. 2024 Aug 30;15(37):15474-9. doi: 10.1039/d4sc02969k.
Developing innovative methodologies for disulfide preparation is of importance in contemporary organic chemistry. Despite significant advancements in nickel-catalyzed reductive cross-coupling reactions for forming carbon-carbon and carbon-heteroatom bonds, the synthesis of S-S bonds remains a considerable challenge. In this context, we present a novel approach utilizing nickel catalysts for the reductive cross-coupling of thiosulfonates. This method operates under mild conditions, offering a convenient and efficient pathway to synthesize a wide range of both symmetrical and unsymmetrical disulfides from readily available, bench-stable thiosulfonates with exceptional selectivity. Notably, this approach is highly versatile, allowing for the late-stage modification of pharmaceuticals and the preparation of various targeted compounds. A comprehensive mechanistic investigation has been conducted to substantiate the proposed hypothesis.
开发用于二硫化物制备的创新方法在当代有机化学中具有重要意义。尽管镍催化的用于形成碳 - 碳键和碳 - 杂原子键的还原交叉偶联反应取得了显著进展，但S - S键的合成仍然是一个相当大的挑战。在此背景下，我们提出了一种利用镍催化剂进行硫代磺酸酯还原交叉偶联的新方法。该方法在温和条件下运行，提供了一条方便且高效的途径，可从易于获得、在实验室稳定的硫代磺酸酯中以优异的选择性合成各种对称和不对称二硫化物。值得注意的是，这种方法具有高度的通用性，允许对药物进行后期修饰并制备各种目标化合物。已进行了全面的机理研究以证实所提出的假设。
